Thionyl Chloride → HCID 178425055, compound

HRID 1898399Notes

Reaction equation

HRID 1898399 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]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[C:39]([F:42])([F:41])[F:40].CCN(C(C)C)C(C)C>C1COCC1.C1C=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]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([F:31])=[C:33]([C:39]([F:42])([F:40])[F:41])[CH:34]=3)=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 178425067HCID 178425067, compound

Product 1

HCID 178425055HCID 178425055, compoundYield 5.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the procedure as 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, 0.150 g, 0.403 mmol), thionyl chloride (2.0 mL), 4-fluoro-3-(trifluoromethyl)aniline (0.108 g, 0.604 mmol), benzene (4 mL), THF (6.0 mL) and DIPEA (4 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 2.24 (s, 3H), 3.10 (s, 2H), 7.30-7.54 (m, 5H), 7.82 (m, 1H), 8.36 (m, 1H), 9.08 (s, 1H), 9.92 (s, 1H), 10.96 (s, 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-4c7108a080c2442f822edcbd3010ce59
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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