Methyl 4-(5-bromothiazolo[5,4-b]pyridin-2-ylcarbamoyl)benzoate → HCID 178497988, compound

HRID 1924773Notes

Reaction equation

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

Participants

Reactant 2

HCID 58015381Methyl 4-(5-bromothiazolo[5,4-b]pyridin-2-ylcarbamoyl)benzoate

HCID 178434487HCID 178434487, compound

Product 1

HCID 178497988HCID 178497988, compoundYield 17%

Procedure

The titled compound (yield=17%, yellow solid) was prepared using a procedure analogous to that described in connection with 9 (Example 9) except 1C (Example 3) 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 2.58 (s, 3H) 3.91 (s, 3H) 6.56 (br. s., 1H) 7.76 (d, J=8.59 Hz, 1H) 8.12 (d, J=8.59 Hz, 4H) 8.25 (d, J=8.59 Hz, 2H) 13.15 (br. s., 1H); ESI-MS: m/z 394.0 (M+H)+.

Sources & evidence

ORD record: ord-884908500e52458fbaaf57398742eee7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

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