Formic Acid → 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

반응식

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][C:13]#[N:14])=[C:6]([NH2:15])[CH:5]=1.[CH:17](O)=O>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][C:13]#[N:14])[CH:17]=[N:15][C:6]=2[CH:5]=1)=[O:16]

참가 물질

반응물 2

HCID 284Formic Acid

HCID 669874673-Amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester

생성물 1

HCID 669871661-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester수율 95%

반응 조건

온도: 50 °C

실험 절차

To 3-amino-4-(2-cyano-ethylamino)-benzoic acid methyl ester (4.0 g) was added formic acid (25 ml) and the mixture heated to 50° C. for 3 h. It was then concentrated and the residue recrystallised from EtOAc to afford 4.0 g (95%) of 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 230 (M+1); 1H NMR (300 MHz, CDCl3) δ 2.95 (t, 2H), 4.0 (s, 3H), 4.55 (t, 2H), 7.4 (d, 1H), 8.1 (m, 1H), 8.15 (s, 1H), 8.55 (s, 1H)

후처리

concentrationIt was then concentrated
customthe residue recrystallised from EtOAc

출처 및 근거

ORD 기록: ord-0eb1abaa14084ba58aae1766aa733892
출처 데이터셋: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08053431B2

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