Water → N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide

HRID 57331노트

반응식

HRID 57331 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH2:17][CH:16]([C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=4[CH:20]=[O:21])[O:15][N:14]=3)[N:12]=2)[CH2:4][CH2:3]1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([N:34]=[C:35]=[O:36])[CH:28]=1.O>ClCCl.C(N(C(C)C)CC)(C)C.N12CCCN=C1CCCCC2>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([NH:34][C:35]([N:2]2[CH2:3][CH2:4][CH:5]([C:8]3[S:9][CH:10]=[C:11]([C:13]4[CH2:17][CH:16]([C:18]5[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=5[CH:20]=[O:21])[O:15][N:14]=4)[N:12]=3)[CH2:6][CH2:7]2)=[O:36])[CH:28]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 27696325-Chloro-2-methylphenyl isocyanateHCID 866652252-{3-[2-(Piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride

생성물 1

HCID 86665224N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide

시약·촉매·용매 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 6344Dichloromethane용매HCID 81531Diisopropylethylamine용매

실험 절차

To a suspension of 2-{3-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride (1.43 g) in dichloromethane (30 ml) and diisopropylethylamine (0.73 ml) were added, at room temperature, 4-chloro-2-isocyanato-1-methylbenzene (700 mg) and one drop of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The mixture was stirred at room temperature overnight, and water was then added. The aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave N-(5-chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide (1.23 g).

후처리

  1. additionwere added, at room temperature
  2. customThe aqueous phase was removed
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-9ccac10e8da74222a4f83fe242efe049
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434723B2

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