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

HRID 1924770Notes

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][C:25]1[C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][NH: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:29]2[C:25]([CH3:24])=[N:26][NH:27][CH:28]=2)[N:7]=3)=[O:23])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

Reactant 2

HCID 58015365N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide

HCID 178434487HCID 178434487, compound

Product 1

HCID 1784345144-(2-hydroxypropan-2-yl)-N-(5-(3-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)benzamideYield 11%

Procedure

The titled compound (yield=11%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 1D (Example 1) and 3-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) 2.58 (s, 3H) 7.66 (d, J=8.59 Hz, 2H) 7.74 (d, J=8.59 Hz, 1H) 8.09 (d, J=8.59 Hz, 4H) 12.86 (s, 1H); ESI-MS: m/z 394.0 (M+H)+.

Sources & evidence

ORD record: ord-f17d35ed75d84c2cbc506fb9d65ee81e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

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