Hydrochloric Acid → HCID 69373683, compound

HRID 1179311Notes

Reaction equation

HRID 1179311 reaction equation
[C:1]([C:3]1[C:8]([NH:9][CH2:10][CH2:11][N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1)#N.[CH3:18][OH:19].Cl.[OH2:21]>>[CH3:17][N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH2:11][CH2:10][NH:9][C:8]1[C:3]([C:1]([O:19][CH3:18])=[O:21])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 58977993Methanesulfonamide, N-[2-[(2-cyano-3-pyridinyl)amino]ethyl]-N-methyl-

Product 1

HCID 69373683HCID 69373683, compound

Procedure

In a manner similar to that described for Example 2, N-{2-[(2-cyanopyridin-3-yl)amino]ethyl}-N-methylmethanesulfonamide was treated with MeOH, HCl and water to give methyl 3-({2-[methyl(methylsulfonyl)amino]ethyl}amino)pyridine-2-carboxylate after aqueous workup. The crude product was then treated with NaH and methyl 3-chloro-3-oxopropionate as described in Example 2 and after aqueous workup the crude methyl 4-hydroxy-1-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate was obtained as a pink foam. A portion of the material was crystallized from EtOH to give the product as light brown crystals.

Sources & evidence

ORD record
ord-bd497131ef2742c2a86bcfd126691a99
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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