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Trifluoroacetic acid → 1-cyclohexyl-2-(3-furyl)-N-[2-(4-hydroxyphenyl)-1-(2-pyridyl)ethyl]benzimidazole-5-carboxamide

HRID 1018257
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HRID 1018257 반응식
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(=N)C1C=CC=CC=1.C(OC([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=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.C(O)(C(F)(F)F)=O>>[OH:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH:2]([NH:1][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:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:31][CH:32]=1
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 6422Trifluoroacetic acidHCID 195092-PyridinemethanamineHCID 428166PhenylmethanimineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 226691824-Tert-butoxycarbonyloxy-benzyl chloride

생성물 1

HCID 490856
1-cyclohexyl-2-(3-furyl)-N-[2-(4-hydroxyphenyl)-1-(2-pyridyl)ethyl]benzimidazole-5-carboxamide

실험 절차

2-(Aminomethyl)pyridine was converted to its benzaldehyde imine (benzaldehyde in DCM with 4A molecular sieves) and alkylated with 4-tert-butoxycarbonyloxy-benzyl chloride following an adaptation of the procedure described by Y. Wang et al. (Synth. Commun. 1992, 22, 265). The resulting racemic amine was coupled to the carboxylic acid of example 2 under the usual conditions, and deprotected with TFA to give the title compound of example 38 after purification by preparative C18 reversed-phase HPLC.

출처 및 근거

ORD 기록
ord-8889f483dc0f4b26a4b2ffd472455761
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479508B1

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