Hydrazine hydrate (1:1) → 1-(4-methyl-5-(1H-pyrazol-5-yl)thiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

HRID 560853노트

반응식

HRID 560853 반응식
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:16]=3)[C:10]2=[O:29])=[N:6][C:5]=1[CH3:30])(=O)[CH3:2].COC(OC)[N:34]([CH3:36])C.O.[NH2:40]N>CN(C)C=O.C(OCC)(=O)C>[CH3:30][C:5]1[N:6]=[C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:22])=[CH:19][CH:20]=3)[C:10]2=[O:29])[S:8][C:4]=1[C:1]1[NH:40][N:34]=[CH:36][CH:2]=1

참가 물질

6

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

생성물 1

HCID 666309441-(4-methyl-5-(1H-pyrazol-5-yl)thiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one수율 54%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one (0.43 g, 1.00 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethyl acetal (0.20 mL, 1.50 mmol). The reaction mixture was heated for 20 hours at 110° C., and hydrazine monohydrate (0.25 mL, 5.14 mmol) was added. The reaction mixture was heated for another 10 minutes at 110° C., then cooled to ambient temperature, diluted with ethyl acetate and washed with water. The organic phase 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 colorless solid in 54% yield (0.26 g): mp 156-157° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 7.45-7.22 (m, 4H), 4.50 (s, 2H), 4.15-4.01 (m, 2H), 3.69-3.32 (m, 6H), 2.60 (s, 3H), 2.40 (s, 3H), 1.71-1.20 (m, 6H): MS (ES+) m/z 427.1 (M+1).

후처리

  1. temperatureThe reaction mixture was heated for another 10 minutes at 110° C.
  2. temperaturecooled to ambient temperature
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-0a965821ffbd4e73b4057bd0c00dcb43
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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