Methylamine hydrochloride → HCID 136107840, compound

HRID 1676973Notes

Reaction equation

HRID 1676973 reaction equation
ClC1C=C2C(=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.[Br:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35](S(C1C=CC=CC=1)(=O)=O)[C:34]([C:48]([O:50]CC)=O)=[C:33]2[S:53](Cl)(=[O:55])=[O:54].Cl.CN.[CH3:60][NH:61][CH2:62][C:63]1[NH:64][C:65](=[O:68])[NH:66][N:67]=1>>[Br:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:48]([NH2:7])=[O:50])=[C:33]2[S:53]([N:61]([CH3:60])[CH2:62][C:63]1[NH:64][C:65](=[O:68])[NH:66][N:67]=1)(=[O:54])=[O:55]

Participants

5

Reactant 4

HCID 6364545Methylamine hydrochlorideHCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylateHCID 135469014HCID 135469014, compound

Product 1

HCID 136107840HCID 136107840, compound

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 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with 5-[(methylamino)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, (prepared using the method of T. Ladduwahetty et al., J. Med. Chem 1996, 39, 2907-2914) the title compound was obtained. Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C13H14BrN6O4S (M+H+): 428.9975. Found 428.9974.

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-18ff16feb4c64aa483d4bb96bf7c0402
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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