1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 4-(2-hydroxypropan-2-yl)-N-(5-(1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 1924772Notes

Reaction equation

HRID 1924772 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:24][N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[N:26]1>>[OH:22][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:28]2[CH:27]=[N:26][N:25]([CH3:24])[CH:29]=2)[N:7]=3)=[O:23])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58015365N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 445489304-(2-hydroxypropan-2-yl)-N-(5-(1-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamideYield 37%

Procedure

The titled compound (yield=37%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 1D (Example 1) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6H) 3.90 (s, 3H) 7.66 (d, J=8.08 Hz, 2H) 7.78 (d, J=8.59 Hz, 1H) 8.04-8.14 (m, 4H) 8.38 (s, 1H) 12.89 (br. s., 1H); ESI-MS: m/z 394.0 (M+H)+.

Sources & evidence

ORD record
ord-3597605fa853413e86dc5dbbe558a7cd
Source dataset
uspto-grants-2012_05
Patent number
US08178555B2

Reaction notes

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