2,6-Difluoropyridine-4-boronic acid → (R)-2',6'-Difluoro-2-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,4'-bipyridine]-5-carboxamide

HRID 924115

反応式

HRID 924115 の反応式
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[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].[F:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[C:31]([F:38])[N:30]=1>>[F:28][C:29]1[CH:34]=[C:33]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[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:32]=[C:31]([F:38])[N:30]=1

参加物

3

反応物 2

HCID 27627472,6-Difluoropyridine-4-boronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

生成物 1

HCID 118195169(R)-2',6'-Difluoro-2-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,4'-bipyridine]-5-carboxamide

実験手順

The title compound was prepared in an analogous fashion to that described in Example 169 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 2,6-difluoropyridin-4-ylboronic acid to afford a white amorphous powder. HPLC (Condition 4) tR=5.67 min, UPLC-MS (Condition 3) tR=1.10 min, m/z=481.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.80 (m, 1H) 1.87 (m, J=9.00 Hz, 1H) 2.86 (d, J=11.34 Hz, 1H) 3.18-3.29 (m, 2H) 3.47 (m, J=7.00 Hz, 1H) 4.22 (br. s, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.23 (s, 2H) 7.34 (d, J=9.38 Hz, 2H) 7.78-7.89 (m, 2H) 8.13 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 10.18 (s, 1H).

後処理

  1. customto afford a white amorphous powder

出典と根拠

ORDレコード
ord-fa83b769f2164fb485d08ffa2cf1a8db
出典データセット
uspto-grants-2016_03
特許番号
US09278981B2

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