4-(Methylcarbamoyl)benzeneboronic acid → 4-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(4-(methylcarbamoyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924777ノート

反応式

HRID 1924777 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25](=[O:37])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[CH:28][CH:27]=3)=[N:23][C:18]2=[CH:17][CH:16]=1>>[OH:34][CH2:33][C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:25]([NH:24][C:22]2[S:21][C:19]3[C:18]([N:23]=2)=[CH:17][CH:16]=[C:15]([C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[NH:2][CH3:1])=[CH:6][CH:7]=2)[N:20]=3)=[O:37])=[CH:27][CH:28]=1)([CH3:36])[CH3:35]

参加物

3

反応物 2

HCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

生成物 1

HCID 445487754-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(4-(methylcarbamoyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)benzamide収率 15%

実験手順

The titled compound (yield=15%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 4-(methylcarbamoyl)phenylboronic acid and 2F (Example 2) were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 2.82 (d, J=4.55 Hz, 3H) 3.49 (d, J=5.31 Hz, 2H) 4.75-4.81 (m, 1H) 7.58 (d, J=8.84 Hz, 2H) 7.98 (d, J=8.59 Hz, 2H) 8.11 (d, J=8.84 Hz, 2H) 8.17-8.22 (m, 1H) 8.22-8.28 (m, 3H) 8.56 (q, J=4.63 Hz, 1H) 13.02 (s, 1H); ESI-MS: m/z 461.0 (M+H)+.

出典と根拠

ORDレコード
ord-523f14ba42e741448ceef54584cacab0
出典データセット
uspto-grants-2012_05
特許番号
US08178555B2

反応ノート

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