Propylamine → HCID 54230793, compound

HRID 850680Notes

Reaction equation

HRID 850680 reaction equation
[CH:1]12[N:7]([C:8](=[O:56])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=3)=[C:15]4[C@H:29]([CH3:55])[CH2:30][N:31]([CH2:47][CH2:48][N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)S(C3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)(=O)=[O:33])([CH3:11])[CH3:10])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C(N)CC>>[OH-:33].[NH4+:7].[CH:4]12[N:7]([C:8](=[O:56])[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][C:16]([C:21]3[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([CH3:27])[CH:26]=3)=[C:15]4[C@H:29]([CH3:55])[CH2:30][NH:31][CH2:47][CH2:48][N:49]3[CH2:50][CH2:51][O:52][CH2:53][CH2:54]3)([CH3:11])[CH3:10])[CH:1]([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 7852PropylamineHCID 54193464HCID 54193464, compound

Product 2

HCID 14923Ammonium HydroxideHCID 54230793HCID 54230793, compoundYield 179.8%

Procedure

To a solution of (S)-N-{2-[5-[2-(7-aza-bicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-N-(2-morpholin-4-yl-ethyl)-2,4-dinitrobenzenesulfonamide (61.3 mg in 1.4 mL dry methylene chloride) was added 0.130 mL of n-propylamine and the mixture stirred at room temperature. After 60 minutes the reaction was quenched by the addition of water, extracted with ethyl acetate and the combined organics washed with saturated aqueous sodium bicarbonate. The organic portion was then dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (methylene chloride:methanol, 92:8; then methylene chloride:methanol:ammonium hydroxide, 90:7:1) gave the title compound (39 mg).

Workup

  1. customAfter 60 minutes the reaction was quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. washthe combined organics washed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic portion was then dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-279f9d8cd01f40ab821a4095cd165f10
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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