Methylamine hydrochloride → Ethyl-5-bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HRID 1676993Notes

Reaction equation

HRID 1676993 reaction equation
ClC1C=C2C(=CC=1)N(S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.Cl[S:30]([C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([Br:42])[CH:40]=2)[N:35]([S:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)(=[O:45])=[O:44])[C:34]=1[C:52]([O:54][CH2:55][CH3:56])=[O:53])(=[O:32])=[O:31].Cl.CN.C(O)(=O)C(O)=O.[NH2:66][CH2:67][CH2:68][CH2:69][CH2:70][C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72]>>[CH2:55]([O:54][C:52]([C:34]1[N:35]([S:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)(=[O:45])=[O:44])[C:36]2[C:41]([C:33]=1[S:30]([NH:66][CH2:67][CH2:68][CH2:69][CH2:70][C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])(=[O:32])=[O:31])=[CH:40][C:39]([Br:42])=[CH:38][CH:37]=2)=[O:53])[CH3:56]

Participants

5

Reactant 4

HCID 6364545Methylamine hydrochlorideHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 85937127tert-Butyl 5-aminopentanoate oxalate(1:x)HCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 67372682Ethyl-5-bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Procedure

Following the procedures described in Steps D and E of Example 1, replacing in Step D ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with tert-butyl 5-aminopentanoate oxalic acid salt, the title compound was obtained after flash chromatography through silica gel (100% dicloromethane). ESI+ MS: 587 [M-CH2═CMe2]+.

Sources & evidence

ORD record
ord-8257d2999af84cc89cb347a08bfdde87
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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