Cyclohexylamine → 2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2,N-dicyclohexyl-acetamide

HRID 889377Notes

Reaction equation

HRID 889377 reaction equation
FC1C(O[C:9](=[O:32])[CH:10]([C:17]2[N:18]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[N:19]=[C:20]3[CH2:24][CH2:23][CH2:22][C:21]=23)[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=C(F)C(F)=C(F)C=1F.[CH:37]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([N:18]2[C:17]([CH:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[C:9]([NH:43][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:32])=[C:21]3[CH2:22][CH2:23][CH2:24][C:20]3=[N:19]2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 86657983[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester

Product 1

HCID 533902542-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2,N-dicyclohexyl-acetamideYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid pentafluorophenyl ester (95 mg, 181 umol) in DMF (0.9 ml) was added cyclohexylamine (30 ul, 271 umol; CAS Reg. No. 108-91-8) and DMAP (66 mg, 543 umol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred at ambient temperature for 30 h. The solvent was removed under reduced pressure to give a brown oil which was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (32 mg, 75 umol; 40%) as brown oil. MS: m/e=440.3 [M+H+].

Workup

  1. customat ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. customto give a brown oil which
  4. customwas purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-17643325fa3e49cfa39541c6f8bfe71f
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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