Stannous chloride dihydrate → 7-iodo-3,3-dimethyl-1H,2H,3H,4H-pyrido[2,3-b]pyrazin-2-one

HRID 659369Notes

Reaction equation

HRID 659369 reaction equation
C[O:2][C:3](=O)[C:4]([NH:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][C:11]([I:17])=[CH:10][N:9]=1)([CH3:6])[CH3:5].O.O.Cl[Sn]Cl>C(O)C>[I:17][C:11]1[CH:10]=[N:9][C:8]2[NH:7][C:4]([CH3:6])([CH3:5])[C:3](=[O:2])[NH:14][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 57885856HCID 57885856, compound

Product 1

HCID 578860407-iodo-3,3-dimethyl-1H,2H,3H,4H-pyrido[2,3-b]pyrazin-2-oneYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(5-Iodo-3-nitro-pyridin-2-ylamino)-2-methyl-propionic acid methyl ester (618 mg) was dissolved in ethanol. SnCl2.2H2O (5 eq) was added and the reaction mixture was heated to 80° C. for three (3) hours. The resulting precipitate was filtered and washed with ethanol to give the title compound as an off-white solid (46% yield). M.p.>300° C., LCMS: m/z=304.30 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.29 (s, 6H), 7.11 (bs, 1H), 7.16 (d, J=1.8 Hz, 1H), 7.80 (d, J=2.0 Hz, 1H), 10.38 (bs, 1H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-2592f7465be54e1f98642a507c6475b3
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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