Propylamine → HCID 15462392, compound

HRID 1603069Notes

Reaction equation

[CH:1]12[N:7]([C:8](=[O:61])[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]([CH3:60])[CH2:30][N:31]([CH2:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([N:55]4[CH:59]=[N:58][N:57]=[CH:56]4)=[CH:51][CH:50]=3)S(C3C=CC([N+]([O-])=O)=CC=3[N+]([O-])=O)(=O)=O)([CH3:11])[CH3:10])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C(N)CC>>[CH:4]12[N:7]([C:8](=[O:61])[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]([CH3:60])[CH2:30][NH:31][CH2:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([N:55]4[CH:59]=[N:58][N:57]=[CH:56]4)=[CH:51][CH:50]=3)([CH3:11])[CH3:10])[CH:1]([CH2:2][CH2:3]1)[CH2:6][CH2:5]2

Participants

Reactant 2

HCID 7852Propylamine

HCID 53972788HCID 53972788, compound

Product 1

HCID 15462392HCID 15462392, compoundYield 100.6%

Procedure

To a solution of (S)-N-{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]propyl}-2,4-dinitro-N-[2-(4-[1,2,4]triazol-4-yl-phenyl)ethyl]benzenesulfonamide (0.246 g in 5.5 mL dry methylene chloride) was added 0.72 mL of n-propylamine and the mixture stirred at room temperature. After 35 minutes the volatiles were removed in vacuo and the concentrate purified by flash chromatography on silica gel (methylene chloride:methanol, 90:10; then 85:15) to give the title compound (0.180 g). MASS: 615 (M+H)

Workup

customAfter 35 minutes the volatiles were removed in vacuo
customthe concentrate purified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record: ord-94d99ff39efe49008117e3e5a5cef248
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05985901

Reaction notes

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