Cyclohexylamine → 2-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamide

HRID 1678620노트

반응식

HRID 1678620 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([OH:20])=O)=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[CH:27]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([NH:33][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:20])=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67131005[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid

생성물 1

HCID 451103842-[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-2,N-dicyclohexyl-acetamide수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an ice cold solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-acetic acid (9 mg, 24 μmol and cyclohexylamine (2.3 μl, 24 μmol; CAS Reg. No. 108-91-8) in CH2Cl2 (1 ml) under an argon atmosphere was added bromotripyrrolidinophosphonium hexafluorophosphate (17 mg, 36 umol) and N,N-diisopropylethylamine (10 ul, 72 umol). The reaction mixture was stirred for 5 d at ambient temperature, poured onto ice water/1 N aqueous NaOH solution 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/1 N aqueous HCl solution 1/1 and brine and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and the residue was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (5 mg, 11 μmol; 46%) as colorless foam. MS: m/e=450.3 [M+H+].

후처리

  1. additionpoured onto ice water/1 N aqueous NaOH solution 1/1
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/1 N aqueous HCl solution 1/1 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customthe residue was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

출처 및 근거

ORD 기록
ord-e645341f91f84e568a94158b4a3fdf23
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008505B2

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