Thionyl Chloride → HCID 178422734, compound

HRID 1898395Notes

Reaction equation

HRID 1898395 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][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([C:39]2([NH2:42])[CH2:41][CH2:40]2)[CH:36]=[CH:37][CH:38]=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:42][C:39]3([C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:31])([F:43])[F:44])[CH:34]=4)[CH2:41][CH2:40]3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 431465831-(3-(Trifluoromethyl)phenyl)cyclopropanamineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422734HCID 178422734, compoundYield 6.7%

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), 1-[3-(trifluoromethyl)phenyl]cyclopropanamine (Intermediate-44, 0.078 g, 0.388 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 0.010 g of the desired product. 1HNMR (DMSO-d6): δ 1.17-1.37 (m, 4H), 1.51 (s, 6H), 3.06 (s, 2H), 7.34-7.51 (m, 8H), 8.39 (s, 1H), 11.00 (2H); MS [M+H]+: 559.16.

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-5d50e25a7eb344bbae8cff4c7cb0bd40
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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