3-Pyridinylboronic acid → 2-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923890

반응식

HRID 923890 반응식
Br[C:2]1[C:3]([N:22]2[CH2:26][C@H:25]([OH:27])[C@@H:24]([OH:28])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1>>[OH:28][C@@H:24]1[C@@H:25]([OH:27])[CH2:26][N:22]([C:3]2[C:2]([C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

참가 물질

3

반응물 2

HCID 27343783-Pyridinylboronic acidHCID 899079005-bromo-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

생성물 1

HCID 1181953272-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

실험 절차

The title compound was prepared in an analogous fashion to that described in Example 75 using 5-bromo-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 70.1) and pyridin-3-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.01 min, m/z=461.1 [M+H]+, m/z=459.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.94 (d, J=11.74 Hz, 2H) 3.37-3.45 (m, 2H) 3.85 (d, J=2.69 Hz, 2H) 5.04 (br. s, 2H) 7.35 (d, J=8.31 Hz, 2H) 7.51 (dd, J=7.09, 4.89 Hz, 1H) 7.81 (d, J=7.83 Hz, 1H) 7.86 (d, 2H) 8.04 (d, J=2.45 Hz, 1H) 8.59 (dd, J=4.77, 1.59 Hz, 1H) 8.64 (d, J=1.96 Hz, 1H) 8.76 (d, J=2.20 Hz, 1H) 10.18 (s, 1H).

후처리

  1. customto afford a white solid

출처 및 근거

ORD 기록
ord-400259c945ed4428b88f1b7dcbb2e027
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278981B2

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