Triethylamine → 1-[2(3,4-Dimethoxyphenyl) thiazol-4-ylcarbonyl]-2-methoxymethyl-4-(3,4,5-trimethoxybenzoyl)piperazine

HRID 358788노트

반응식

HRID 358788 반응식
Cl.[CH3:2][O:3][CH2:4][CH:5]1[CH2:10][N:9]([C:11](=[O:24])[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH2:8][CH2:7][NH:6]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:35]2[S:36][CH:37]=[C:38]([C:40](O)=[O:41])[N:39]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:35]2[S:36][CH:37]=[C:38]([C:40]([N:6]3[CH2:7][CH2:8][N:9]([C:11](=[O:24])[C:12]4[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=4)[CH2:10][CH:5]3[CH2:4][O:3][CH3:2])=[O:41])[N:39]=2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14737902-(3,4-dimethoxyphenyl)-1,3-thiazole-4-carboxylic AcidHCID 200666662-Methoxymethyl-4-(3,4,5trimethoxybenzoyl)piperazine hydrochloride

생성물 1

HCID 216252151-[2(3,4-Dimethoxyphenyl) thiazol-4-ylcarbonyl]-2-methoxymethyl-4-(3,4,5-trimethoxybenzoyl)piperazine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 2-methoxymethyl-4-(3,4,5trimethoxybenzoyl) piperazine hydrochloride obtained in Reference Example 6 (0.50 g), 2-(3,4-dimethoxyphenyl)thiazol-4-carboxylic acid (0.37 g), triethylamine (0.42 g) and N,N-dimethylformamide (5 ml) is added dropwise, while stirring under icecooling, diethyl cyanophosphonate (0.46 g). The reaction mixture is stirred at 0° C. for one hour and there poured into ice-water, followed by extraction with ethyl acetate. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is purified by means of a silica gel column chromatography (eluent: AcOEt) to give 1-[2(3,4-dimethoxyphenyl) thiazol-4-ylcarbonyl]-2-methoxymethyl-4-(3,4,5-trimethoxybenzoyl)piperazine. Recrystallization from EtOH gives colorless needles, m.p. 149-151° C.

후처리

  1. additionis added dropwise
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate is purified by means of a silica gel column chromatography (eluent: AcOEt)

출처 및 근거

ORD 기록
ord-6dda10ce77a74ea6a9a69fb6ac58c0ad
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997836

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