Thionyl Chloride → HCID 178422800, compound

HRID 1898384Notes

Reaction equation

HRID 1898384 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])[O:33][C:34]1[N:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=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]([CH3:22])([CH3:23])[O:21][C:17]=3[C:16]([C:24]([NH:40][C:37]3[CH:38]=[N:39][C:34]([O:33][CH:32]([F:41])[F:31])=[CH:35][CH:36]=3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 450909846-(Difluoromethoxy)pyridin-3-amineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422800HCID 178422800, compoundYield 14.5%

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), 6-(difluoromethoxy)pyridin-3-amine (Intermediate-36, 0.065 g, 0.399 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 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.09 (s, 2H), 7.12 (d, J=8.7 Hz, 1H), 7.30-7.46 (m, 4H), 7.66 (s, 1H), 7.90 (s, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.59 (s, 1H), 9.79 (s, 1H), 11.20 (s, 1H); MS [M+H]+: 518.24.

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-a99a5019070e48fdb5b293876dc6778a
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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