Cyclopentylamine → HCID 25181769, compound

HRID 1510435Notes

Reaction equation

HRID 1510435 reaction equation
[C:1]([C:3]1[C:4]([C:18]([O:20]CC)=O)=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)#[N:2].[CH:23]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)C>[C:1]([C:3]1[C:4]([C:18]([NH:28][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:20])=[N:5][O:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=1)#[N:2]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 67121104HCID 67121104, compound

Product 1

HCID 25181769HCID 25181769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
82 °C

Procedure

A mixture of ethyl 4-cyano-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (150 mg, 0.48 mmol) and cyclopentylamine (0.24 mL, 2.4 mmol) in ethanol (5 mL) was heated to 82° C. for 16 hours. The volatiles were removed in vacuo and the residue was purified by silica gel chromatography, eluting with 5% methanol in dichloromethane to afford the title compound: (130 mg, 0.37 mmol). 1H NMR (300 MHz, CDCl3) δ 8.27 (m, 2H), 7.86 (m, 2H), 6.68 (br. d, 1H), 4.43 (m, 1H), 2.11 (m, 2H), 1.85-1.45 (m, 6H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ab83b760901b479a8a8a588b371f75fa
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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