5-Amino-2-(trifluoromethyl)pyridine → 2-((2-Chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-N-(6-(trifluoromethyl)pyridin-3-yl)-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]3[CH2:17][C:18]([CH3:28])([CH3:27])[O:19][C:20]=3[C:21]([C:23]([O:25]C)=O)=[CH:22][C:12]=2[N:11]=1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:38])[F:37])=[N:34][CH:35]=1.C[Al](C)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]3[CH2:17][C:18]([CH3:27])([CH3:28])[O:19][C:20]=3[C:21]([C:23]([NH:29][C:30]3[CH:35]=[N:34][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:32][CH:31]=3)=[O:25])=[CH:22][C:12]=2[N:11]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared by following the same procedure as described for Example-137 using methyl 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (step-7 of Intermediate-49, 0.100 g, 0.247 mmol), 5-amino-2-trifloromethylpyridine (0.162 g, 0.371 mmol), trimethyl aluminium (2M solution in toluene) (1 mL) to afford 0.025 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.46 (s, 2H), 3.57 (s, 3H), 7.01 (m, 1H), 7.28 (s, 2H), 7.30 (d, 1H), 7.90 (d, J=8.7 Hz, 1H), 8.45 (d, J=7.8 Hz, 1H), 9.00 (s, 1H), 10.02 (s, 1H), 10.53 (s, 1H). MS [M−H]−: 532.19.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-b5d24c9cbb8b403da936e53a76897464
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519149B2
Reaction notes
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