Thionyl Chloride → HCID 178422776, compound

HRID 1898386Notes

Reaction equation

HRID 1898386 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[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])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=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[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:36][C:35]3[CH:37]=[CH:38][C:32]([F:31])=[CH:33][C:34]=3[C:39]([F:42])([F:40])[F:41])=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 678534-Fluoro-2-(trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422776HCID 178422776, compoundYield 28%

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-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.100 g, 0.266 mmol), thionyl chloride (2.0 mL), 4-fluoro-2-(trifluoromethyl)aniline (0.095 g, 0.530 mmol), THF (10.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on neutral alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.040 g of the desired product. 1HNMR (DMSO-d6): δ 1.53 (s, 6H), 3.12 (s, 2H), 7.34-7.41 (m, 4H), 7.60-7.67 (m, 2H), 8.40 (m, 1H), 10.02 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 537.17.

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-97fe3753d9ba4aa2812cae765b62835f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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