hydrogen chloride CPME → 2'-chloro-N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)biphenyl-4-carboxamide hydrochloride

HRID 922540Notes

Reaction equation

HRID 922540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C@@H:23]3[CH2:25][C@H:24]3[N:26]([CH2:34][CH:35]3[CH2:37][CH2:36]3)C(=O)OC(C)(C)C)=[CH:19][CH:18]=2)=[O:15])=[CH:10][CH:9]=1.Cl.COC1CCCC1>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C@@H:23]3[CH2:25][C@H:24]3[NH:26][CH2:34][CH:35]3[CH2:37][CH2:36]3)=[CH:21][CH:22]=2)=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 66926893hydrogen chloride CPMEHCID 86729906tert-Butyl [trans-2-(4-{[(2'-chlorobiphenyl-4-yl)carbonyl]amino}phenyl)cyclopropyl](cyclopropylmethyl)-carbamate

Product 1

HCID 867299042'-chloro-N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)biphenyl-4-carboxamide hydrochlorideYield 128.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl [trans-2-(4-{[(2′-chlorobiphenyl-4-yl)carbonyl]amino}phenyl)cyclopropyl](cyclopropylmethyl)-carbamate (115 mg) was dissolved in THF (0.5 mL), and the mixture was ice-cooled to 0° C. 4N Hydrochloric acid/cyclopentyl methyl ether solution (5 mL) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure. The residue was recrystallized from methanol/diisopropyl ether to give the title compound (65.0 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was recrystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-a5a9329d8a6244cb913d5ad74dc789b4
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

Loading…