3-(Trifluoromethyl)aniline → HCID 178425401, compound

HRID 1898391Notes

Reaction equation

HRID 1898391 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][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)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:34]=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][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:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:31])([F:40])[F:41])[CH:34]=3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178425402HCID 178425402, compound

Product 1

HCID 178425401HCID 178425401, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure described for Example-108 using 2-[(2-chloro-5-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-27, 0.175 g, 0.471 mmol), thionyl chloride (2.0 mL), 3-trifluoromethyl phenyl amine (0.114 g, 0.707 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 0.9% MeOH:DCM to afford 0.040 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 2.33 (s, 3H), 3.16 (d, J=5.4 Hz, 2H), 6.87-6.88 (m, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.44 (d, J=7.2 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.73 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 8.34 (s, 2H), 9.00 (s, 1H), 10.01 (s, 1H), 10.05 (s, 1H); MS [M+H]+: 515.22.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on neutral alumina eluting with 0.9% MeOH

Sources & evidence

ORD record
ord-e2aeb04798984a66a39d2040ec15aac3
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…