(3-Fluoro-4-((2-hydroxyethyl)carbamoyl)phenyl)boronic acid → 2-Fluoro-N-(2-hydroxy-ethyl)-4-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzamide

HRID 1470382

반응식

HRID 1470382 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[O:10][C:3]=12.[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[C:30](=[O:35])[NH:31][CH2:32][CH2:33][OH:34]>>[F:23][C:24]1[CH:25]=[C:26]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[O:10][C:3]=23)[CH:27]=[CH:28][C:29]=1[C:30]([NH:31][CH2:32][CH2:33][OH:34])=[O:35]

참가 물질

3

실험 절차

The title compound was prepared by procedure C using 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine (45.00 mg; 0.14 mmol; 1.00 eq.) instead of 7-chloro-2-iodo-furo[3,2-b]pyridine, and 3-fluoro-4-[(2-hydroxyethyl)-carbamoyl]benzeneboronic acid (35.14 mg; 0.15 mmol; 1.10 eq.) instead of 4-fluorophenylboronic acid and was obtained as a pale yellow solid (32 mg, 48%). (HPLC (method F): 99%, RT: 3.09 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.60 (dd, J=5.1, 1.8, 1H), 8.38 (s, 1H), 8.12-8.06 (m, 2H), 7.89 (t, J=7.9, 1H), 7.79 (d, J=1.8, 1H), 7.71 (dd, J=5.1, 1.8, 1H), 7.33 (d, J=1.7, 2H), 4.80-4.73 (m, 1H), 3.92 (d, J=1.7, 6H), 3.74 (d, J=1.8, 3H), 3.57-3.51 (m, 2H), 3.37 (dd, J=12.0, 6.1, 2H); MS (m/z) 467 [M+H]+, RT: 3.0 min.

출처 및 근거

ORD 기록
ord-73643c79f4094314aeffdd8057cc2f0c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006440B2

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