Cyclopentylamine → HCID 178523891, compound

HRID 2280409Notes

Reaction equation

HRID 2280409 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([NH:20][C:21]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=S)[NH:17][N:16]=2)=[C:11]([F:36])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH:48]1([NH2:53])[CH2:52][CH2:51][CH2:50][CH2:49]1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([NH:20][C:21]([NH:53][CH:48]3[CH2:52][CH2:51][CH2:50][CH2:49]3)=[N:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[NH:17][N:16]=2)=[C:11]([F:36])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178523934HCID 178523934, compound

Product 1

HCID 178523891HCID 178523891, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-((3-(4-(Benzyloxy)-2-fluorophenyl)-1H-pyrazol-5-yl)carbamothioyl)-4-(trifluoromethyl)benzamide (154 mg, 0.3 mmol) and EDCI (63 mg, 0.33 mmol) were suspended in THF (4 mL) and cyclopentylamine (0.044 mL, 0.45 mmol) was added. The resulting mixture was stirred at 50° C. for 45 minutes, then concentrated onto silica gel and purified by chromatography (gradient: 9:1 hexanes:EtOAc to 6:4 hexanes:EtOAc) to provide the title compound in 53% yield.

Workup

  1. concentrationconcentrated onto silica gel
  2. custompurified by chromatography (gradient: 9:1 hexanes:EtOAc to 6:4 hexanes:EtOAc)

Sources & evidence

ORD record
ord-713d145dc451402daf2afff4a4a28e67
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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