Thionyl Chloride → HCID 178425065, compound

HRID 1898378Notes

Reaction equation

HRID 1898378 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)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[C:33]=1[NH2:34].CCN(C(C)C)C(C)C>C1COCC1>[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]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:34][C:33]3[C:32]([F:31])=[CH:38][C:37]([F:39])=[CH:36][C:35]=3[F:40])=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 677652,4,6-TrifluoroanilineHCID 81531DiisopropylethylamineHCID 178425067HCID 178425067, compound

Product 1

HCID 178425065HCID 178425065, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure described for Example-108 using 2-[(2-chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-35, 0.100 g, 0.268 mmol), thionyl chloride (3.0 mL), 2,4,6-trifluoroaniline (0.059 g, 0.403 mmol), THF (10.0 mL) and DIPEA (3 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.52 (s, 6H), 2.24 (s, 3H), 3.10 (s, 2H), 7.24-7.32 (m, 4H), 7.41 (d, J=7.2 Hz, 1H), 7.45 (s, 1H), 9.12 (s, 1H), 10.91 (s, 1H); MS [M+H]+: 501.37.

Workup

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

Sources & evidence

ORD record
ord-300169fc513e4c0db1351037c58ec3fe
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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