Thionyl Chloride → HCID 178422750, compound

HRID 1898388Notes

Reaction equation

HRID 1898388 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]([C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38])([F:34])[CH3:33].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]=[CH:40][CH:41]=[C:35]([C:32]([F:31])([F:34])[CH3:33])[CH:36]=3)=[O:26])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 234450923-(1,1-Difluoroethyl)anilineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422750HCID 178422750, compoundYield 6.6%

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, 0.273 g, 0.736 mmol), thionyl chloride (2.0 mL), 3-(1,1-difluoroethyl)aniline (Intermediate-39, 0.120 g, 0.736 mmol), THF (5.0 mL) and DIPEA (3 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.025 g of the desired product. 1HNMR (DMSO d6): δ 1.57 (s, 6H), 1.97 (t, J=19.2 Hz, 3H), 3.10 (s, 2H), 7.26-7.32 (m, 3H), 7.35-7.48 (m, 3H), 7.62 (d, J=8.4 Hz, 1H), 8.07 (s, 1H), 9.85 (s, 1H), 11.00 (s, 2H); MS [M−H]−: 513.14.

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-e653688905a944c69526e5979315abd5
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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