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

HRID 358787
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HRID 358787 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.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[S:32][CH:33]=[C:34]([C:36](O)=[O:37])[N:35]=2)[CH:26]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O>[CH3:2][O:3][CH2:4][CH:5]1[CH2:10][N:9]([C:11](=[O:24])[C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[CH2:8][CH2:7][N:6]1[C:36]([C:34]1[N:35]=[C:31]([C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[S:32][CH:33]=1)=[O:37]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 7365132-(3-Pyridyl)thiazole-4-carboxylic acidHCID 200666662-Methoxymethyl-4-(3,4,5trimethoxybenzoyl)piperazine hydrochloride

생성물 1

HCID 541996132-Methoxymethyl-1-[2-(3-pyridyl) thiazol-4-ylcarbonyl]-4-(3,4,5-trimethoxybenzoyl) piperazine

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

To a mixture of 2-methoxymethyl-4-(3,4,5trimethoxybenzoyl)piperazine hydrochloride obtained in Reference Example 6 (0.52 g), 2-(3-pyridyl)thiazol-4-carboxylic acid (0.3 g), triethylamine (0.46 g) and N,N-dimethylformamide (3 ml) is added dropwise, while stirring under icecooling, diethyl cyanophosphonate (0.47 g). The reaction mixture is stirred at 0° C. for one hour, and then 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-CH2Cl2 --CH3OH=10:9:1) to give 2-methoxymethyl-1-[2-(3-pyridyl) thiazol-4-ylcarbonyl]-4-(3,4,5-trimethoxybenzoyl) piperazine. Recrystallization from ethanol gives colorless needles m.p. 149-150° 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-CH2Cl2 --CH3OH=10:9:1)

출처 및 근거

ORD 기록
ord-47ba3f47be074ffcb2c99fc9a0fa8e5d
출처 데이터셋
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04997836

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