Triethylamine → CID 49843530

HRID 1618116ノート

反応式

HRID 1618116 の反応式
[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:21](=[O:22])[C:20]4[C:19]([C:23](O)=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[C@@H:14]3[CH3:26])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].OC1C2N=N[NH:34]C=2C=CC=1.C(N(CC)CC)C>O1CCCC1>[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:21](=[O:22])[C:20]4[C:19]([C:23]([NH2:34])=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[C@@H:14]3[CH3:26])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 67191867(1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acidHCID 178515910HCID 178515910、化合物

生成物 1

HCID 49843530CID 49843530収率 40.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid (0.15 gr, 0.42 mmol), hydroxybenzotriazole ammonium salt (0.13 gr, 0.84 mmol) and 1-ethyl-3-(3′-dimethylamino) carbodiimide hydrochloric acid salt (0.16 gr, 0.84 mmol) were dissolved in a mixture of tetrahydrofuran (6 mL) and triethylamine (0.23 mL, 1.68 mmol) and stirred under nitrogen atmosphere for 16 hours. Volatiles were evaporated and the crude was dissolved in dichloromethane and washed with 15% ammonium hydroxide. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude was purified by flash chromatography (dichloromethane/methanol/7N ammonia in methanol 100:3:1) to afford the title compound (0.060 g, 40%) as a white solid.

後処理

  1. customVolatiles were evaporated
  2. dissolutionthe crude was dissolved in dichloromethane
  3. washwashed with 15% ammonium hydroxide
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography (dichloromethane/methanol/7N ammonia in methanol 100:3:1)

出典と根拠

ORDレコード
ord-5e3f0c81e928431dad67a5939a76e775
出典データセット
uspto-grants-2014_07
特許番号
US08765972B2

反応ノート

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