Sodium hydride → HCID 66571463、化合物

HRID 83646

反応式

HRID 83646 の反応式
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:42][CH2:43][O:44][CH3:45])(=O)=O)=CC=1>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH2:42][CH2:43][O:44][CH3:45])[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

生成物 1

HCID 66571463HCID 66571463、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) dissolved in 0.5 mL of DMF was added to a suspension of sodium hydride (7.99 mg, 0.200 mmol) in 1.0 mL of DMF. The reaction was heated at 70° C. for ten minutes before adding 2-methoxyethyl 4-methylbenzenesulfonate (0.144 mL, 0.266 mmol). The reaction was allowed to stir overnight. After 18 hours, the reaction was cooled to room temperature before diluting with water and ethyl acetate. The organic phase was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via column chromatography using 50-80% ethyl acetate/hexanes. The purification provided product as a white solid 1H-NMR (400 MHz, DMSO-d6) 7.63-7.49, 7.43-7.14, 7.12-7.03, 6.67-6.58, 4.68, 4.63-4.06, 3.53, 3.20-3.13, 3.10-2.92, 2.79, 1.92-1.50

後処理

  1. waitAfter 18 hours
  2. temperaturethe reaction was cooled to room temperature
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified via column chromatography
  8. customThe purification

出典と根拠

ORDレコード
ord-d3af2161ee3b470897c7471e4f176c77
出典データセット
uspto-grants-2014_09
特許番号
US08846684B2

関連ノート

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