4-(Trifluoromethyl)aniline → HCID 67503518, compound

HRID 1898404Notes

Reaction equation

HRID 1898404 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:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1.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:38][C:37]3[CH:39]=[CH:40][C:34]([C:33]([F:32])([F:41])[F:42])=[CH:35][CH:36]=3)=[O:24])=[CH:22][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 99644-(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 67503518HCID 67503518, compoundYield 7.3%

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, 0.2564 mmol), thionyl chloride (2.0 mL), 4-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 0.010 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.47 (s, 3H), 3.56 (s, 2H), 7.17-7.01 (m, 1H), 7.21 (bs, 2H), 7.29 (d, J=8.4 Hz, 1H), 7.70 (d, J=8.4 Hz, 2H), 7.90 (d, J=7.8 Hz, 2H), 9.92 (bs, 1H), 10.52 (bs, 1H): MS [M+H]+: 533.25.

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-5bf65ab98f9b4801abfe04f5a47bec18
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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