2,4,5-Trifluoroaniline → HCID 178425064, compound

HRID 1898457Notes

Reaction equation

HRID 1898457 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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]([O:26]C)=O)=[CH:15][C:13]=2[N:14]=1.[F:28][C:29]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[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]([NH:31][C:30]3[CH:32]=[C:33]([F:37])[C:34]([F:36])=[CH:35][C:29]=3[F:28])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 949532,4,5-TrifluoroanilineHCID 16682925TrimethylaluminumHCID 178496983HCID 178496983, compound

Product 1

HCID 178425064HCID 178425064, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the procedure described for Example-137 by using methyl 2-[(2-chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-35, 0.200 g, 0.414 mmol) and 2,4,5-trifluoroaniline (0.090 g, 0.602 mmol), trimethyl aluminium (2M solution in toluene) (1 mL) and dry toluene (5.0 mL) to afford 0.070 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 2.24 (s, 3H), 3.17 (s, 2H), 7.25-7.33 (m, 2H), 7.42 (d, J=8.80 Hz, 1H), 7.52 (s, 1H), 7.72 (q, J=8.4 Hz, 10.8 Hz, 1H), 8.48-8.58 (m, 1H), 9.13 (br s, 1H), 10.16 (s, 1H), 10.98 (br s, 1H): MS [M+H]+: 501.0

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-5688c84058bd4326a978d2f52f46638d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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