Acetone → HCID 57576744, compound

HRID 599432Notes

Reaction equation

HRID 599432 reaction equation
[CH3:1][C:2]([CH3:4])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:28][O:29][NH2:30])[N:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[C:14]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>CO>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:28][O:29][N:30]=[C:2]([CH3:4])[CH3:1])[N:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[C:14]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 67052331HCID 67052331, compound

Product 1

HCID 57576744HCID 57576744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetone (1 mL) was added to a solution of the N-(3-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}propyl)-2-methylpropanamide from Part I in methanol (10 mL). The reaction mixture was allowed to stir overnight at room temperature. The volatiles were removed under reduced pressure and the residue was purified by chromatography on a HORIZON HPFC system (silica gel, 0-25% CMA in chloroform) to afford 0.495 g of N-{3-[4-amino-2-({[(1-methylethylidene)amino]oxy}methyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propyl}-2-methylpropanamide as off-white needles, mp 195-197° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by chromatography on a HORIZON HPFC system (silica gel, 0-25% CMA in chloroform)

Sources & evidence

ORD record
ord-88a40fe6d37f476890771ab982280b93
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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