5-Amino-2-(trifluoromethyl)pyridine → HCID 178422772, compound

HRID 1898432Notes

Reaction equation

HRID 1898432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](OC)=[O:25])=[CH:15][C:13]=2[N:14]=1.[F:28][C:29]([F:38])([F:37])[C:30]1[N:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1.C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:36][C:33]3[CH:34]=[N:35][C:30]([C:29]([F:38])([F:28])[F:37])=[CH:31][CH:32]=3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 16682925TrimethylaluminumHCID 178496985HCID 178496985, compound

Product 1

HCID 178422772HCID 178422772, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-137 using methyl 2-[(2,6-dichlorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-6, 0.200 g, 0.493 mmol) and 6-(trifluoromethyl)pyridin-3-amine (0.119 g, 0.740 mmol), trimethyl aluminium (2M solution in toluene) (0.071 g, 0.986 mmol) and dry toluene (5.0 mL) to afford 0.100 g of the desired product. 1HNMR (DMSO-d6): δ 1.58 (s, 6H), 3.09 (s, 2H), 7.39 (m, 3H), 7.53 (m, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.46 (d, J=9.0 Hz, 1H), 8.99 (s, 1H), 10.07 (s, 1H), 10.94 (s, 2H); MS [M]+: 536.17.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-319c37e722b447d6ae54afebfaf7426b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…