6-(Hydroxymethyl)pyridine-3-boronic acid → 6'-(Hydroxymethyl)-2-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923889

반응식

HRID 923889 반응식
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][CH2:24][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].[OH:27][CH2:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[OH:27][CH2:28][C:29]1[N:34]=[CH:33][C:32]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:4][CH:5]=[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:21]=2)=[CH:31][CH:30]=1

참가 물질

3

반응물 2

HCID 441182556-(Hydroxymethyl)pyridine-3-boronic acidHCID 899068675-bromo-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

생성물 1

HCID 1181953586'-(Hydroxymethyl)-2-(pyrrolidin-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 66 using 5-bromo-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 67.1) and (6-(hydroxymethyl)pyridin-3-yl)boronic acid to afford a white solid. UPLC-MS (Condition 3) tR=1.0 min, m/z=459.2 [M+H]+, m/z=456.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.84 (m, 4H) 3.05-3.21 (m, 4H) 4.62 (br. s, 2H) 5.50 (br. s, 1H) 7.34 (d, J=8.78 Hz, 2H) 7.54 (d, J=8.03 Hz, 1H) 7.81 (dd, J=8.03, 2.26 Hz, 1H) 7.83-7.89 (m, 2H) 8.01 (d, J=2.38 Hz, 1H) 8.51-8.55 (m, 1H) 8.76 (d, J=2.38 Hz, 1H) 10.18 (s, 1H).

후처리

  1. customto afford a white solid

출처 및 근거

ORD 기록
ord-2bc614946c2b4e25aa9a6b2a7a75bb27
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278981B2

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