4-Methylmorpholine → HCID 86656649, compound

HRID 882901Notes

Reaction equation

HRID 882901 reaction equation
[Br-:1].[NH2:2][CH2:3][CH2:4][CH2:5][N+:6]([CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:19]([NH2:20])=[N:18][C:17]([NH2:21])=[C:16]([Cl:22])[N:15]=1)=[O:13])([CH3:8])[CH3:7].[C:23]1([CH3:34])[CH:28]=[CH:27][C:26]([CH2:29][S:30](Cl)(=[O:32])=[O:31])=[CH:25][CH:24]=1.CN1CCOCC1>CN(C=O)C>[Br-:1].[NH2:20][C:19]1[C:14]([C:12]([NH:11][CH2:10][CH2:9][N+:6]([CH3:7])([CH3:8])[CH2:5][CH2:4][CH2:3][NH:2][S:30]([CH2:29][C:26]2[CH:27]=[CH:28][C:23]([CH3:34])=[CH:24][CH:25]=2)(=[O:32])=[O:31])=[O:13])=[N:15][C:16]([Cl:22])=[C:17]([NH2:21])[N:18]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2794648(4-Methylphenyl)methanesulfonyl chlorideHCID 86656637HCID 86656637, compound2×

Product 1

HCID 86656649HCID 86656649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (3-amino-propyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate M) (0.30 g, 0.756 mmol), p-tolyl-methanesulfonyl chloride (0.16 g, 0.76 mmol) and N-methylmorpholine (0.4 mL, 3.64 mmol) in DMF (5 mL) is shaken at RT for 16 h. The solvent is removed in vacuo and the residue is subjected to chromatography (basic alumina; 0-15% methanol in DCM) to yield the title compound. M+ 484.

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7cc82e90977046b3a4474e5c6fef4ed9
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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