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Trifluoroacetic acid → 2-(3,5-dimethylphenyl)-3-[2-(1-methyl-4-pyridin-3-yl-butylamino)ethyl]-1H-indole-5-carboxylic acid diisobutylamide

HRID 1458362
ノート
印刷プレビュー

反応式

HRID 1458362 の反応式
[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH2:27])=[O:7])[CH:2]([CH3:4])[CH3:3].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][CH2:39][CH2:40][C:41](=O)[CH3:42])[CH:33]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([N:5]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[CH2:25][CH2:26][NH:27][CH:41]([CH3:42])[CH2:40][CH2:39][CH2:38][C:34]1[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6422Trifluoroacetic acid2 回HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 137397405-(3-Pyridinyl)-2-pentanoneHCID 537946513-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

生成物 1

HCID 67664720
2-(3,5-dimethylphenyl)-3-[2-(1-methyl-4-pyridin-3-yl-butylamino)ethyl]-1H-indole-5-carboxylic acid diisobutylamide
収率 48.5%

実験手順

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide (142 mg in dry methanol) was added 19 mg 5-pyridin-3-yl-pentan-2-one and the pH adjusted to 6 by the addition of trifluoroacetic acid. To this, approximately 10 mg of 3 Å molecular sieves were added followed by 27 mg of sodium cyanoborohydride. The pH was adjusted occasionally with trifluoroacetic acid over 36 hours to maintain pH of 6. The reaction was then quencehed by the addition of aqueous potassium carbonate and the mixture extracted with ethyl acetate. The organic portion was washed sequentially with aqueous potassium carbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1) gave the title compound (32 mg) [m/e =567 (M+H)] plus unreacted amine (115 mg).

後処理

  1. additionTo this, approximately 10 mg of 3 Å molecular sieves were added
  2. temperatureto maintain pH of 6
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic portion was washed sequentially with aqueous potassium carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1)

出典と根拠

ORDレコード
ord-b17f16c81c9f4a138f6f2a0fde11c7b8
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849764

反応ノート

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