Acetonitrile → HCID 21069800, compound

HRID 348214Notes

Reaction equation

HRID 348214 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:27]=1[C:28]([O:30]C)=[O:29])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC#N.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:27]=1[C:28]([OH:30])=[O:29])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 21069968HCID 21069968, compound

Product 1

HCID 21069800HCID 21069800, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of intermediate 154, methyl 2-((3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamido)methyl)-5-fluorobenzoate. (500 mg, 1.01 mmol) in MeOH (10 mL) and CH3CN (5 mL) was added 1N NaOH (2 mL) and the mixture stirred at room temperature for 2 hrs. The mixture was concentrated in vacuo and the residue purified by reverse phase column chromatography (YMC, C-18 ODS, 10–25% CH3CN/H2O) to provide 90 mg (Yield 19%) of the title compound as an off-white powder: LC/MS m/z 482 (M+H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by reverse phase column chromatography (YMC, C-18 ODS, 10–25% CH3CN/H2O)

Sources & evidence

ORD record
ord-429a936206f44fa49d55c4b9f3ccc3a1
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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