3-(Trifluoromethyl)aniline → HCID 67503476, compound

HRID 1898405Notes

Reaction equation

HRID 1898405 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]([CH3:27])([CH3:26])[O:19][C:20]=3[C:21]([C:23](O)=[O:24])=[CH:22][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[F:32][C:33]([F:42])([F:41])[C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37].CCN(C(C)C)C(C)C>C1COCC1>[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]([CH3:26])([CH3:27])[O:19][C:20]=3[C:21]([C:23]([NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[C:34]([C:33]([F:32])([F:41])[F:42])[CH:35]=3)=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 675027202-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic Acid

Product 1

HCID 67503476HCID 67503476, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-108 using 2-((2-chloro-6-fluorophenyl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylic acid (Intermediate-49, 0.100 g, 0.256 mmol), thionyl chloride (2.0 mL), 3-trifluoromethyl aniline (0.124 g, 0.769 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.46 (s, 2H), 3.56 (s, 3H), 7.00 (m, 1H), 7.20 (m, 2H), 7.28 (d, 2H), 7.28 (d, 1H), 7.45 (d, 1H), 7.56 (t, 1H), 7.75 (d, J=7.2 Hz, 1H), 8.31 (s, 1H), 9.98 (s, 1H), 10.51 (s, 1H); MS [M+H]+: 533.27.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH

Sources & evidence

ORD record
ord-507aa92df7dd49cf8264532cff742196
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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