Thionyl Chloride → HCID 178422785, compound

HRID 1898397Notes

Reaction equation

HRID 1898397 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](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][CH:32]([F:41])[C:33]1[CH:34]=[CH:35][C:36]([F:40])=[C:37]([CH:39]=1)[NH2:38].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]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:38][C:37]3[CH:39]=[C:33]([CH:32]([F:31])[F:41])[CH:34]=[CH:35][C:36]=3[F:40])=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 675035275-(Difluoromethyl)-2-fluoroanilineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422785HCID 178422785, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by following the same procedure as 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, 0.150 g, 0.400 mmol), thionyl chloride (2.0 mL), 5-(difluoromethyl)-2-fluoroaniline (Intermediate-46, 0.097 g, 0.600 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 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.56 (s, 6H), 3.13 (s, 2H), 7.07 (t, J=55.5 Hz, 1H), 7.33-7.52 (m, 6H), 8.76 (d, J=6.9 Hz, 1H), 10.24 (s, 1H), 11.20 (s, 2H); MS [M+H]+: 519.20.

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-b25606bd9236485289d099d67513d7ba
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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