Triethylamine → 2,N-Dicyclohexyl-2-(2-phenyl-2H-indazol-3-yl)-acetamide

HRID 1678611Notes

Reaction equation

C1(N[C:8]2[N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)CCCCC1.CC[N:25]([CH2:28][CH3:29])CC.[CH:30]1([CH2:36][C:37](Cl)=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(Cl)(Cl)Cl>[CH:30]1([CH:36]([C:8]2[N:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)[C:37]([NH:25][CH:28]2[CH2:29][CH2:13][CH2:12][CH2:11][CH2:16]2)=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of cyclohexyl-(2-phenyl-2H-indazol-3-yl)-amine (30 mg, 103 μmol) in chloroform was added Et3N (16 μl, 113 μmol) and cyclohexylacetylchloride (16 μl, 108 μmol; CAS Reg. No. 23860-35-7) at ambient temperature under an argon atmosphere. The mixture was heated to 80° C. for 12 h, poured onto ice water/1 N HCl 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/1 N NaOH 1/1 and ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and the crude product was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (27 mg, 65 μmol; 63%) as colorless foam. MS: m/e=416.5 [M+H+].

Workup

customat ambient temperature
extractionextracted two times with iPrOAc
washThe combined extracts were washed with ice water/1 N NaOH 1/1 and ice water/brine 1/1
dry with materialdried over Na2SO4
filtrationAfter filtration the solvent
customwas removed under reduced pressure
customthe crude product was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record: ord-ad036d75ff6b40839fc7e46e63a59d26
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008505B2

Reaction notes

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