2-(dimethylamino)acetohydrazide -Drug Synthesis Database

【结构式】

【分子编号】40924

【品名】2-(dimethylamino)acetohydrazide

【CA登记号】539-64-0

【分子式】C₄H₁₁N₃O

【分子量】117.15096

【元素组成】C 41.01% H 9.46% N 35.87% O 13.66%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：

A new synthesis of adinazolam has been described: The condensation of phthaloyl-glycyl chloride (I) with 2-amino-5-chlorobenzophenone (II) in refluxing toluene gives 4-chloro-2-(phthaloylglycylamido)benzophenone (III), which is cyclized by means of hydrazine in refluxing ethanol yielding 7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (IV). The reaction of (IV) with P2S5 in hot pyridine affords the corresponding thione (V), which is finally cyclized with N,N-dimethylglycine hydrazide by means of triethylamine in refluxing butanol. The starting products (I) and (II) are obtained as follows: The reaction of N-(ethoxycarbonyl)phthalimide (VI) with glycine by means of Na2CO3 in water gives the N-phthaloylglycine (VII), which is then treated with refluxing SOCl2 to give (I). The protection of 2-amino-4-chlorobenzoic acid (VIII) with tosyl chloride gives the corresponding N-tosyl derivative (IX), which by reaction with refluxing SOCl2 is converted into the acyl chloride (X). Finally, this compound is submitted to a Friedel-Craft's condensation with benzene and AlCl3 to afford (II).

参考文献中间体

合成目标

【1】 Johnson, T.D.; Hsi, R.S.P.; Carbon-14 labeled 1,4-benzodiazepines. 3. J Label Compd Radiopharm 1976, 12, 4, 613-619.
【2】 Castaner, J.; Pento, J.T.; Blancafort, P.; Serradell, M.N.; Adinazolam. Drugs Fut 1983, 8, 2, 87.
【3】 Stelzer, L.S.; Hsi, R.S.P.; Synthesis of adinazolam mesylate-multiply labeled with carbon-13 and deuterium. J Label Compd Radiopharm 1989, 26, 3, 287.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	13364	Benzene	71-43-2	C₆H₆	详情	详情
	40924	2-(dimethylamino)acetohydrazide	539-64-0	C₄H₁₁N₃O	详情	详情
(I)	10278	2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride	6780-38-7	C₁₀H₆ClNO₃	详情	详情
(II)	10279	(2-Amino-5-chlorophenyl)(phenyl)methanone; 2-Amino-5-chlorobenzophenone	719-59-5	C₁₃H₁₀ClNO	详情	详情
(III)	10280	N-(2-Benzoyl-4-chlorophenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide		C₂₃H₁₅ClN₂O₄	详情	详情
(IV)	10281	7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 1,4-benzdiazepin-2-one-5-phenyl-7-chloro	1088-11-5	C₁₅H₁₁ClN₂O	详情	详情
(V)	10282	7-Chloro-5-phenyl-3H-1,4-benzodiazepin-2-ylhydrosulfide; 7-Chloro-5-phenyl-3H-1,4-benzodiazepine-2-thiol		C₁₅H₁₁ClN₂S	详情	详情
(VI)	10283	ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide	22509-74-6	C₁₁H₉NO₄	详情	详情
(VII)	10284	N-Phthaloylglycine; 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid	4702-13-0	C₁₀H₇NO₄	详情	详情
(VIII)	10285	2-Amino-5-chlorobenzoic acid	635-21-2	C₇H₆ClNO₂	详情	详情
(IX)	10286	5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid		C₁₄H₁₂ClNO₄S	详情	详情
(X)	10287	5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoyl chloride		C₁₄H₁₁Cl₂NO₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Swern oxidation of the sulfonyl dipeptide alcohol (I) in the presence of sulfur trioxide-pyridine complex and DMSO affords aldehyde (II). This is then condensed with (dimethylamino)acetohydrazide (III) to produce the target N-acyl hydrazone

参考文献中间体

合成目标

【1】 Nakamura, M.; Inoue, J.; Exploration of peptidyl hydrazones as water-soluble calpain inhibitors. Bioorg Med Chem Lett 2002, 12, 12, 1603.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	57913	(2S)-2-{[(4-fluorophenyl)sulfonyl]amino}-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-3-methylbutanamide		C₁₇H₂₇FN₂O₄S	详情	详情
(II)	60378	(2S)-2-{[(4-fluorophenyl)sulfonyl]amino}-N-[(1S)-1-formyl-3-methylbutyl]-3-methylbutanamide		C₁₇H₂₅FN₂O₄S	详情	详情
(III)	40924	2-(dimethylamino)acetohydrazide	539-64-0	C₄H₁₁N₃O	详情	详情

Extended Information