1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-{3-[4-(4-Chlorophenyl)-2-propyl-5-oxazolyl]propanoyl}-4-[(1-methyl-4-piperidinyl)methyl]piperazine dihydrochloride

HRID 350756노트

반응식

HRID 350756 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][CH:3]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:42][N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[CH2:45][CH2:44]1>O.CN(C)C=O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([N:53]2[CH2:52][CH2:51][N:50]([CH2:49][CH:46]3[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]3)[CH2:55][CH2:54]2)=[O:17])=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 210886803-[4-(4-Chlorophenyl)-2-propyl-5-oxazolyl]propionic acid

생성물 1

HCID 210884481-{3-[4-(4-Chlorophenyl)-2-propyl-5-oxazolyl]propanoyl}-4-[(1-methyl-4-piperidinyl)methyl]piperazine dihydrochloride수율 96.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-[4-(4-chlorophenyl)-2-propyl-5-oxazolyl]propionic acid (41.7 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (41 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (46 mg), 4-[(1-methyl-4-piperidinyl)methyl]piperazine (60 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, introduced into preparative HPLC and purified. To the obtained oil was added ethyl acetate, and the mixture was washed with saturated aqueous sodium hydrogen carbonate. A 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer and the mixture was concentrated to give 1-{3-[4-(4-chlorophenyl)-2-propyl-5-oxazolyl]propanoyl}-4-[(1-methyl-4-piperidinyl)methyl]piperazine dihydrochloride (25.0 mg, yield 32%). Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 218° c (dec.).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified
  5. additionTo the obtained oil was added ethyl acetate
  6. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate
  7. additionA 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer
  8. concentrationthe mixture was concentrated

출처 및 근거

ORD 기록
ord-ae6ebdd9ee974e1da7c45bd88a0ebcad
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183276B2

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