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 1458351Notes

Reaction equation

HRID 1458351 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-1db3e2d4cccb44e0908acf71673d16b4
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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