2-Methoxypyrimidine-5-boronic acid → 4-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(2-methoxypyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924778Notes

Reaction equation

HRID 1924778 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:24])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]1[N:32]=[CH:31][C:30](B(O)O)=[CH:29][N:28]=1>>[OH:21][CH2:20][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][C:9]2[S:8][C:6]3[C:5]([N:10]=2)=[CH:4][CH:3]=[C:2]([C:30]2[CH:29]=[N:28][C:27]([O:26][CH3:25])=[N:32][CH:31]=2)[N:7]=3)=[O:24])=[CH:14][CH:15]=1)([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

Product 1

HCID 445487744-(1-hydroxy-2-methylpropan-2-yl)-N-(5-(2-methoxypyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl)benzamideYield 33%

Procedure

The titled compound (yield=33%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 2F (Example 2) and 2-methoxypyrimidin-5-yl boronic acid were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (s, 6H) 3.49 (d, J=5.05 Hz, 2H) 4.01 (s, 3H) 4.78 (t, J=5.31 Hz, 1H) 7.58 (d, J=8.59 Hz, 2H) 8.10 (d, J=8.59 Hz, 2H) 8.16 (d, J=8.59 Hz, 1H) 8.22-8.29 (m, 1H) 9.33 (s, 2H) 13.02 (s, 1H); ESI-MS: m/z 436.0 (M+H)+.

Sources & evidence

ORD record
ord-eb37b1fa342d495ea7edba8a162ba83b
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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