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Benzylamine → Racemic 1-cyclohexyl-2-furan-3-yl-1H-benzimidazole-5-carboxylic acid [2-(4-hydroxy-phenyl)-1-phenyl-ethyl]-amide

HRID 1007698
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인쇄 미리보기

반응식

HRID 1007698 반응식
[CH:1](=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O:21]C(OC(Cl)C1C=CC=CC=1)=O)(C)(C)C.[CH:33]1([N:39]2[C:43]3[CH:44]=[CH:45][C:46]([C:48](O)=[O:49])=[CH:47][C:42]=3[N:41]=[C:40]2[C:51]2[CH:55]=[CH:54][O:53][CH:52]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1>[OH:21][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:1]([NH:8][C:48]([C:46]2[CH:45]=[CH:44][C:43]3[N:39]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[C:40]([C:51]4[CH:55]=[CH:54][O:53][CH:52]=4)=[N:41][C:42]=3[CH:47]=2)=[O:49])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7504BenzylamineHCID 428166PhenylmethanimineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 67113782Tert-butoxycarbonyloxy-benzyl chloride

생성물 1

HCID 23378163Racemic 1-cyclohexyl-2-furan-3-yl-1H-benzimidazole-5-carboxylic acid [2-(4-hydroxy-phenyl)-1-phenyl-ethyl]-amide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Following the general method of example 37, the benzaldehyde imine of benzylamine was alkylated with tert-butoxycarbonyloxy-benzyl chloride using lithium hexamethyldisilizane as a base at low temperature (−78° C.) in THF as solvent. Following the usual work up, the racemic amine was coupled to the carboxylic acid of example 2, to give after removal of the Boc group and purification by preparative C18 reversed-phase HPLC, the title compound of example 39.

후처리

  1. customto give
  2. customafter removal of the Boc group and purification by preparative C18 reversed-phase HPLC

출처 및 근거

ORD 기록
ord-f603a3f303404afe8d7851f2ef962baf
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06794404B2

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