2-Methyl-2H-indazol-6-amine → 2-[(2-Bromo-pyridin-4-ylmethyl)-amino]-6-fluoro-N-(2-methyl-2H-indazol-6-yl)-benzamide

HRID 2100430Notes

Reaction equation

HRID 2100430 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4]([O:6]C)=O.[Br:13][C:14]1[CH:19]=[C:18]([CH:20]=O)[CH:17]=[CH:16][N:15]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]2[C:30]([CH:31]=1)=[N:29][N:28]([CH3:32])[CH:27]=2>>[Br:13][C:14]1[CH:19]=[C:18]([CH2:20][NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=2[C:4]([NH:22][C:23]2[CH:24]=[CH:25][C:26]3[C:30]([CH:31]=2)=[N:29][N:28]([CH3:32])[CH:27]=3)=[O:6])[CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 5902202-Methyl-2H-indazol-6-amineHCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 2818492Methyl 2-amino-6-fluorobenzoate

Product 1

HCID 231189892-[(2-Bromo-pyridin-4-ylmethyl)-amino]-6-fluoro-N-(2-methyl-2H-indazol-6-yl)-benzamide

Procedure

2-[(2-Bromo-pyridin-4-ylmethyl)-amino]-6-fluoro-N-(2-methyl-2H-indazol-6-yl)-benzamide was prepared from methyl 2-amino-6-fluorobenzoate via reductive amination with 2-bromo-pyridine-4-carbaldehyde, followed by subsequent amidation with 6-amino-2-methyl-indazole in analogy to the procedures detailed in WO2004/013102, particularly Example 6A, supra; 1H-NMR (300 MHz, d6-DMSO) 10.51 (1H, s), 8.31 (1H, d), 8.26-8.28 (2H, m), 7.65 (1H, d), 7.59 (1H, s), 7.40 (1H, d), 7.13-7.25 (2H, m), 6.73 (1H, t), 6.50 (1H, t), 6.29 (1H, d), 4.47 (2H, d), 4.13 (3H, s).

Sources & evidence

ORD record
ord-6a746255efc44babbd69c1426b7a4f68
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

Loading…