Imidazole → 4-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

HRID 2110044노트

반응식

HRID 2110044 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]([N:23]1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=[S:17].N1C=CN=C1.N[C:34]1[CH:39]=[CH:38]C=C[C:35]=1[CH2:40][C:41]([NH2:43])=[O:42]>C(#N)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([NH:23][C:27]2[CH:26]=[CH:38][CH:39]=[CH:34][C:35]=2[CH2:40][C:41](=[O:42])[NH2:43])=[S:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 2782862-(2-Aminophenyl)acetamideHCID 7368171-Boc-4-(aminomethyl)piperidine

생성물 1

HCID 866105084-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

After dissolving 1-N-Boc-4-aminomethylpiperidine (869 mg, 4.06 mmol) in acetonitrile (10 mL), a solution of thiocarbonyldiimidazole (794 mg, 4.46 mmol) and imidazole (82.9 mg, 1.22 mmol) in acetonitrile (15 mL) was added dropwise in an ice bath, and the mixture was stirred at room temperature for 4 hours. After then adding 2-(2-aminophenyl)acetamide (670 mg, 4.46 mmol) thereto, the mixture was stirred overnight at 60° C. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1) to obtain the title compound.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1)

출처 및 근거

ORD 기록
ord-221f31db34c942319a3cb7052eb6bed2
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517875B2

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