Sodium Carbonate → 3-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid N'-[2-(4-fluoro-phenyl)-acetyl]-hydrazide

HRID 222623Notes

Reaction equation

HRID 222623 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[C:21]([NH:23][NH2:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39](Cl)=[O:40])=[CH:34][CH:33]=1>O1CCCC1>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]([NH:24][NH:23][C:21]([C:10]2[N:11]=[C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:22])=[O:40])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 37449884-Fluorophenylacetyl chlorideHCID 593929043-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid hydrazide

Product 1

HCID 593928983-Benzyloxy-7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid N'-[2-(4-fluoro-phenyl)-acetyl]-hydrazideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 9.1 (160 mg, 0.524 mmol) and sodium carbonate (106 mg, 1 mmol) were mixed with anhydrous tetrahydrofuran (25 mL) and then cooled in ice bath. To this stirred solution was added 4-fluorophenylacetyl chloride (90 mg, 0.55 mmol) dropwise. The mixture was stirred at room temperature for 2 h then concentrated in vacuo. The residue was portioned between ethyl acetate and water and the organic phase washed with water, dried (Na2SO4) and concentrated in vacuo. Short column chromatography afforded the desired compound (210 mg, yield 86%)

Workup

  1. temperaturecooled in ice bath
  2. concentrationthen concentrated in vacuo
  3. washthe organic phase washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0490cf15eb3f4ea9bd0e5545987bb478
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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