Hydrazine hydrate (1:1) → HCID 178423567, 화합물

HRID 560854노트

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HRID 560854 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].CO[C:33](OC)([N:35](C)C)[CH3:34].O.[NH2:41]N>CN(C)C(=O)C.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[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)=[O:22])=[CH:19][CH:20]=3)[C:10]2=[O:29])[S:8][C:4]=1[C:1]1[NH:41][N:35]=[C:33]([CH3:34])[CH:2]=1

참가 물질

6

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

생성물 1

HCID 178423567HCID 178423567, 화합물수율 46%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

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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-dimethylacetamide (5 mL) was added N,N-dimethylacetamide dimethyl acetal (0.5 mL, 3.40 mmol). The reaction mixture was heated for 24 hours at 110° C., and hydrazine monohydrate (0.30 mL, 6.18 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 46% yield (0.25 g): mp 182-183° C. (ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 7.38-7.30 (m, 4H), 6.16 (s, 1H), 4.49 (s, 2H), 4.10-4.04 (m, 2H), 3.68 (br s, 2H), 3.46-3.31 (m, 4H), 2.46 (s, 3H), 2.32 (s, 3H), 1.56-1.49 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 169.9, 156.6, 155.8, 143.6, 137.3, 136.1, 128.2, 127.4, 104.2, 48.7, 47.7, 41.8, 26.5, 25.6, 24.5, 21.1, 16.5: MS (ES+) m/z 465.2 (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-504eb39c800843909f18a0fab9365d7b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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