Acetic Acid → HCID 86689370, compound

HRID 1622922Notes

Reaction equation

HRID 1622922 reaction equation
CO[C:3]([C:5]1[N:6]([CH2:31][CH:32]=O)[CH:7]=[C:8]([C:20](=[O:30])[NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:9](=[O:19])[C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].CO[CH2:36][CH2:37][NH2:38].[C:39](O)(=O)C>C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][NH:21][C:20]([C:8]2[C:9](=[O:19])[C:10]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[C:5]3[C:3](=[O:4])[N:38]([CH2:37][CH2:36][CH3:39])[CH:32]=[CH:31][N:6]3[CH:7]=2)=[O:30])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 596005723-Benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1-(2-oxo-ethyl)-1,4-dihydro-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 86689370HCID 86689370, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 16 (400 mg, 0.884 mmol) in methylene chloride (12 ml) were added 2-methoxyethylamine (77 ul, 0.884 mmol) and acetic acid (18 ul), and the mixture was stirred at room temperature for 5 minutes. Thereafter, the reaction was performed at 140° C. for 30 minutes in a microwave reaction apparatus. The solvent was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography, and fractions eluting with toluene-acetone were concentrated under reduced pressure to obtain 9-benzyloxy-2-(2-methyl-ethyl)-1,8-dioxo-1,8-dihydro-2H-pyrido[1,2-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide 17-1 (226 mg, 54%) as a yellow solid.

Workup

  1. customThereafter, the reaction was performed at 140° C. for 30 minutes in a microwave reaction apparatus
  2. distillationThe solvent was distilled off under reduced pressure
  3. washeluting with toluene-acetone
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff16f1fae8c54778a350b3babc192cee
Source dataset
uspto-grants-2014_07
Patent number
US08778943B2

Reaction notes

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