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

HRID 889377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889377
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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+].

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-17643325fa3e49cfa39541c6f8bfe71f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252826B2

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