N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide → HCID 178434513, compound

HRID 1924774Notes

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][C:26]1[C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][NH:28][N:27]=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[C:26]([CH3:25])=[N:27][NH:28][CH:29]=2)[N:7]=3)=[O:24])=[CH:14][CH:15]=1)([CH3:23])[CH3:22]

Participants

Reactant 2

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

HCID 178434487HCID 178434487, compound

Product 1

HCID 178434513HCID 178434513, compoundYield 20%

Procedure

The titled compound (yield=20%, white solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 2F (Example 2) 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 1.27 (s, 6H) 2.59 (br. s., 3H) 3.49 (br. s., 2H) 7.57 (d, J=8.34 Hz, 2H) 7.74 (d, J=8.59 Hz, 1H) 8.02 (br. s., 1H) 8.05-8.13 (m, 3H) 12.86 (s, 1H); ESI-MS: m/z 408.0 (M+H)+.

Sources & evidence

ORD record: ord-fc872f7b4797403f8345e47a36d55a37
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

Loading…