Phenylacetic Acid → N-benzyl-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-4-methylthiazole-5-carboxamide

HRID 2381869노트

반응식

HRID 2381869 반응식
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38](=[N:40]O)[NH2:39])=[N:35][C:34]=1[CH3:42])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O.ClCCl>[CH2:23]([NH:30][C:31]([C:33]1[S:37][C:36]([C:38]2[N:40]=[C:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:10][N:39]=2)=[N:35][C:34]=1[CH3:42])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 999Phenylacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 136404881N-benzyl-2-(N'-hydroxycarbamimidoyl)-4-methylthiazole-5-carboxamide

생성물 1

HCID 59179717N-benzyl-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-4-methylthiazole-5-carboxamide수율 6.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of phenylacetic acid (0.05 g, 0.37 mmol) in N,N-dimethylformamide (2 mL) was added 1,1′-carbonyldiimidazole (0.14 g, 0.83 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, and N-benzyl-2-(N′-hydroxy-carbamimidoyl)-4-methylthiazole-5-carboxamide (0.12 g, 0.41 mmol) was added. The reaction mixture was stirred for 17 hours, diluted with dichloromethane, washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white powder (0.01 g, 6%): mp 124-125° C.; 1H NMR (300 MHz, CDCl3) δ 7.45-7.25 (m, 10H), 6.16 (t, J=5.6 Hz, 1H), 4.60 (d, J=5.6 Hz, 2H), 4.29 (s, 2H), 2.76 (s, 3H); MS (ES+) m/z 391.5 (M+1).

후처리

  1. stirringThe reaction mixture was stirred for 17 hours
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-618c7a85116e4dff9ed9c208b974e253
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258160B2

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