N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(2-hydroxypropan-2-yl)benzamide → HCID 178458471, compound

HRID 1924775Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[C:7](B(O)O)=[CH:6][NH:5][N:4]=1.Br[C:14]1[N:19]=[C:18]2[S:20][C:21]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]([OH:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)=[N:22][C:17]2=[CH:16][CH:15]=1>>[OH:34][C:31]([C:28]1[CH:27]=[CH:26][C:25]([C:24]([NH:23][C:21]2[S:20][C:18]3[C:17]([N:22]=2)=[CH:16][CH:15]=[C:14]([C:7]2[C:3]([C:2]([F:12])([F:11])[F:1])=[N:4][NH:5][CH:6]=2)[N:19]=3)=[O:35])=[CH:30][CH:29]=1)([CH3:32])[CH3:33]

Participants

Reactant 2

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

HCID 178514840HCID 178514840, compound

Product 1

HCID 178458471HCID 178458471, compoundYield 7%

Procedure

The titled compound (yield=7%) was prepared using a procedure analogous to that described in connection with 10 (Example 10) except 3-(trifluoromethyl)-1H-pyrazol-4-ylboronic acid and 1D (Example 1) were used as starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (s, 6H) 7.67 (d, J=8.34 Hz, 2H) 7.76 (d, J=8.34 Hz, 1H) 8.11 (d, J=8.34 Hz, 2H) 8.20 (d, J=8.59 Hz, 1H) 8.57 (s, 1H) 12.97 (s, 1H) 13.88 (br. s., 1H); ESI-MS: m/z 448.0 (M+H)+.

Sources & evidence

ORD record: ord-6e64e795c67b43e5bd4fd55a4a8ce745
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

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