Propylamine → HCID 9894724, compound

HRID 1275056Notes

Reaction equation

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

Participants

Reactant 2

HCID 7852Propylamine

HCID 53909999HCID 53909999, compound

Product 2

HCID 14923Ammonium Hydroxide

HCID 9894724HCID 9894724, compoundYield 149.1%

Procedure

To a solution of (S)-N-{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-N-(2-imidazo[4,5-b]pyridin-3-yl-ethyl)-2,4-dinitrobenzenesulfonamide (1.5 g in 15 mL dry methylene chloride) was added 1.5 mL of n-propylamine and the mixture stirred at room temperature. After 30 minutes the volatiles were removed in vacuo and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane 1:1; then 4:1; then methylene chloride:methanol:ammonium hydroxide, 95:4:1) to give the title compound (0.804 g).

Workup

customAfter 30 minutes the volatiles were removed in vacuo
customthe concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane 1:1

Sources & evidence

ORD record: ord-2f206277318a45a4bec87057052387bd
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159975

Reaction notes

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