HCID 68755180, compound → HCID 178517020, compound

HRID 1615279Notes

Reaction equation

HRID 1615279 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]/[C:13]1[CH:21]=[C:20]2[C:16]([C:17](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[N:18][N:19]2COCC[Si](C)(C)C)=[CH:15][CH:14]=1>CO.CCO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]/[C:13]1[CH:21]=[C:20]2[C:16]([C:17](/[CH:30]=[CH:31]/[C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)=[N:18][NH:19]2)=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 68755180HCID 68755180, compound

Product 1

HCID 178517020HCID 178517020, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (E)-5-bromo-3-((3-((E)-2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (75 mg, 0.131 mmol) in 12 mL of a 2:1:1 mixture of MeOH/EtOH/4M HCl was heated to 80° C. for 24 hours. LC-MS indicated a mixture of the title compound plus a partially deprotected methoxymethyl indazole compound (see Example A63). The solvents were removed and the mixture was purified by prep-HPLC to give 7.3 mg (13%) of the title compound as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 13.87 (s, 1H), 10.82 (s, 1H), 8.76 (d, J=5.78 Hz, 2H), 8.45 (d, J=8.00 Hz, 1H), 8.23-8.13 (m, 3H), 8.04 (s, 1H), 7.96 (s, 1H), 7.73 (d, J=16.6 Hz, 1H), 7.64 (s, 1H), 7.60 (d, J=7.81 Hz, 1H), 7.43 (d, J=7.31 Hz, 1H), 6.87 (d, J=8.11 Hz, 1H); MS ESI 443.3 [M+H]+, calcd for [C23H15BrN4O+H]+ 443.05.

Sources & evidence

ORD record
ord-8aed1135a55e49d5b2e88f43c6373e69
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…