2-Aminopyridine-3-carboxamide → HCID 135899198, compound

HRID 2100504Notes

Reaction equation

HRID 2100504 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].CO[C:13](=O)[CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][O:15][CH2:14][C:13]2[NH:6][C:4](=[O:5])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[N:1]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 5066232-Aminopyridine-3-carboxamideHCID 2733832Lithium HexamethyldisilazideHCID 67099252[2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl ester

Product 1

HCID 135899198HCID 135899198, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-amino-nicotinamide (250 mg, 1.82 mmol) and [2-(3-fluoro-phenyl)-ethoxy]-acetic acid methyl ester (464 mg, 2.18 mmol) in THF (5 ml) was treated with LiHMDS (1M THF solution, 4.6 ml) overnight at ambient temperature. The yellow suspension was filtrated, the filtrate was brought to dryness and the residue was purified by column chromatography (amino-phase silica gel, CH2Cl2/MeOH, 19/1) to give 2-[2-(3-fluoro-phenyl)-ethoxymethyl]-3H-pyrido[2,3-d]pyrimidin-4-one (303 mg, 1 mmol; 55%) as white solid. MS (m/e): 300.2 [M+H]+

Workup

  1. filtrationThe yellow suspension was filtrated
  2. customthe residue was purified by column chromatography (amino-phase silica gel, CH2Cl2/MeOH, 19/1)

Sources & evidence

ORD record
ord-83bbf18ddbb443179660ee0a8c4a151e
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

Loading…