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Sulfuric acid magnesium salt (1:1) → 2-(3,5-dimethylphenyl)-3-{2-[4-(3-methylisoxazol-5-yl)butylamino]-ethyl-}-1H-indole-5-carboxylic acid diisobutylamide

HRID 1458351
ノート
印刷プレビュー

反応式

HRID 1458351 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].S([O-])([O-])(=O)=O.[Mg+2].[CH3:38][C:39]1[CH:43]=[C:42]([CH2:44][CH2:45][CH2:46][CH:47]=O)[O:41][N:40]=1.[BH4-].[Na+]>>[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][CH2:47][CH2:46][CH2:45][CH2:44][C:42]1[O:41][N:40]=[C:39]([CH3:38])[CH:43]=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

5

反応物 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 221009094-(3-Methylisoxazol-5-yl)-butyraldehydeHCID 537946513-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide

生成物 1

HCID 676668572-(3,5-dimethylphenyl)-3-{2-[4-(3-methylisoxazol-5-yl)butylamino]-ethyl-}-1H-indole-5-carboxylic acid diisobutylamide

実験手順

To a solution of 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide (prepared essentially as described in Example 5.1, 83 mg in 2.5 mL dry CDCl3) at 0° C. was added 240 mg magnesium sulfate followed by 30.6 mg 4-(3-methylisoxazol-5-yl)-butyraldehyde and the mixture stirred at low temperature. After 15 minutes, a cold solution of sodium borohydride (30.2 mg in 1.5 mL dry methanol) was added and the mixture stirred for an additional 15 minutes. At this time the reaction was quenched by the addition of water, extracted with ethyl acetate then methylene chloride and the combined organics dried over sodium sulfate. Purification of the concentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1) gave the title compound (28 mg). m/e=557 (M+H)

後処理

  1. customat 0° C.
  2. stirringthe mixture stirred for an additional 15 minutes
  3. customAt this time the reaction was quenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. dry with materialmethylene chloride and the combined organics dried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1)

出典と根拠

ORDレコード
ord-1db3e2d4cccb44e0908acf71673d16b4
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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