1-Hydroxybenzotriazole → 1-(tert-Butoxycarbonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazine

HRID 278569노트

반응식

HRID 278569 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[S:18][C:19]=1[C:20](O)=[O:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:20]([C:19]2[S:18][C:17]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:16][C:15]=2[CH3:14])=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 14837132-(4-Pyridyl)-4-methylthiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 226279351-(tert-Butoxycarbonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazine수율 83.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a mixture of 1-(tert-butoxycarbonyl)piperazine (3.72 g), 4-methyl-2-(4-pyridyl) -5-thiazolecarboxylic acid (4.4 g), triethylamine (2.5 g) and HOBt (2.7 g) in DMF (60 ml), was added WSC hydrochloride (4.217 g) under ice-cooling and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and to the residue were added dichloromethane and sodium bicarbonate aqueous solution. The organic layer was separated, washed with water and brine, dried and concentrated. The residue was purified with silica gel chromatography (dichloromethane:methanol=50:1) to give colorless crystals of the title compound (6.49 g).

후처리

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. additionto the residue were added dichloromethane and sodium bicarbonate aqueous solution
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel chromatography (dichloromethane:methanol=50:1)

출처 및 근거

ORD 기록
ord-4f931e0184544f0a9af673cd3fc97461
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359134B1

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