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 560853ノート

反応式

HRID 560853 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0a965821ffbd4e73b4057bd0c00dcb43
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

反応ノート

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