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 350756ノート

反応式

HRID 350756 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-ae6ebdd9ee974e1da7c45bd88a0ebcad
出典データセット
uspto-grants-2007_02
特許番号
US07183276B2

反応ノート

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