2-Amino-5-(trifluoromethyl)pyridine → 2-((2-Chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-N-(5-(trifluoromethyl)pyridin-2-yl)-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898423Notes

Reaction equation

HRID 1898423 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](OC)=[O:24])=[CH:22][C:12]=2[N:11]=1.[F:29][C:30]([F:39])([F:38])[C:31]1[CH:32]=[CH:33][C:34]([NH2:37])=[N:35][CH:36]=1.C[Al](C)C>C1(C)C=CC=CC=1>[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]([NH:37][C:34]3[CH:33]=[CH:32][C:31]([C:30]([F:38])([F:29])[F:39])=[CH:36][N:35]=3)=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 16682925TrimethylaluminumHCID 67503529methyl 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate

Product 1

HCID 675033212-((2-Chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-N-(5-(trifluoromethyl)pyridin-2-yl)-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the 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) and 5-(trifluoromethyl)pyridin-2-amine (0.053 g, 0.371 mmol), trimethyl aluminium (2M solution in toluene) (1 mL) and dry toluene (5.0 mL) to afford 0.025 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.49 (s, 2H), 3.57 (s, 3H), 7.17-7.31 (m, 4H), 8.22 (d, J=9 Hz, 1H), 8.44 (d, J=9 Hz, 1H), 8.75 (s, 1H), 8.79 (s, 1H), 10.39 (s, 1H), 10.55 (s, 1H); MS [M+H]+: 534.21.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cb67d73c152546d29c57b9a2676d1e0d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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