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【结 构 式】

【分子编号】63697

【品名】1,1-dimethylethyl 4-aminocyclohexyl(methyl)carbamate

【CA登记号】

【 分 子 式 】C12H24N2O2

【 分 子 量 】228.33484

【元素组成】C 63.12% H 10.59% N 12.27% O 14.01%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(V)

1,4-Diaminocyclohexane (I) is converted into the mono-carbamate (II) employing di-tert-butyl dicarbonate in cold THF. Subsequent reduction of carbamate (II) by means of LiAlH4 leads to the N-methyl amine (III). After blocking the primary amino group of (III) as the corresponding benzaldimine (IV), treatment with di-tert-butyl dicarbonate gives rise to the mono-protected diamine (V). (1,2)

1 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.E. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 6613798; US 6683108; WO 0174344 .
2 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.; Stibbard, J.H.A. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 2002198236; WO 0327234 .
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) 43407 4-aminocyclohexylamine; 1,4-cyclohexanediamine 3114-70-3 C6H14N2 详情 详情
(II) 43408 tert-butyl 4-aminocyclohexylcarbamate C11H22N2O2 详情 详情
(III) 63695 N~1~-methyl-1,4-cyclohexanediamine C7H16N2 详情 详情
(IV) 63696 N~1~-methyl-N~4~-(phenylmethylidene)-1,4-cyclohexanediamine C14H20N2 详情 详情
(V) 63697 1,1-dimethylethyl 4-aminocyclohexyl(methyl)carbamate C12H24N2O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

Suzuki coupling between 2-methoxy-5-formylphenylboronic acid (VI) and 4-bromobenzonitrile (VII) affords the biphenyl aldehyde (VIII). This is then reductively condensed with amine (V) in the presence of NaBH(OAc)3 to furnish (IX). Acylation of amine (IX) with 3-chlorobenzo[b]thiophene-2-carbonyl chloride (X) leads to amide (XI). The N-Boc protecting group of (XI) is finally removed with ethanolic HCl to provide the title compound. (1,2)

1 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.E. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 6613798; US 6683108; WO 0174344 .
2 Baxter, A.D.; Boyd, E.A.; Price, S.; Guicherit, O.M.; Porter, J.; Rubin, L.; Stibbard, J.H.A. (Curis, Inc.); Small organic molecule regulators of cell proliferation. US 2002198236; WO 0327234 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 63697 1,1-dimethylethyl 4-aminocyclohexyl(methyl)carbamate C12H24N2O2 详情 详情
(VI) 63698 5-formyl-2-(methyloxy)phenylboronic acid C8H9BO4 详情 详情
(VII) 45833 4-Bromobenzonitrile 623-00-7 C7H4BrN 详情 详情
(VIII) 63699 3'-formyl-6'-(methyloxy)[1,1'-biphenyl]-4-carbonitrile C15H11NO2 详情 详情
(IX) 63700   C27H35N3O3 详情 详情
(X) 63701 3-chloro-1-benzothiophene-2-carbonyl chloride C9H4Cl2OS 详情 详情
(XI) 63702 1,1-dimethylethyl 4-([(3-chloro-1-benzothiophen-2-yl)carbonyl]{[4'-cyano-6-(methyloxy)[1,1'-biphenyl]-3-yl]methyl}amino)cyclohexyl(methyl)carbamate C36H38ClN3O4S 详情 详情
Extended Information