4-Methylmorpholine → HCID 58147995, compound

HRID 1879927Notes

Reaction equation

HRID 1879927 reaction equation
FC1C=CC(CC(=O)[CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]3[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[CH:29][N:17]3[C:18](=[O:28])[C:19]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])=CC=1.CN1CC[O:44][CH2:43]C1.ClC(OCC)=O.CN(C)O>C1COCC1.C(Cl)Cl>[CH3:43][O:44][N:11]([CH3:10])[C:12]([C:14]1[N:15]=[C:16]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:29][N:17]2[C:18](=[O:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:13]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 27970DimethylhydroxylamineHCID 66953276HCID 66953276, compound2×

Product 1

HCID 58147995HCID 58147995, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-12 °C

Procedure

3-Benzyloxy-7-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid (product of example 5, 100 mg, 0.263 mmol) was dissolved in THF (1 mL) and DCM (11 mL) and cooled to −20° C. N-Methylmorpholine (30 μL, 0.265 mmol) was added and the temperature was raised to −12° C. Ethyl chloroformate was added and after 2 minutes, the solution of dimethylhydroxylamine. The reaction was warmed to room temperature and stirred for one hour. After this time, the mixture was quenched by addition of 0.2 M HCl. The layers were separated and the organic layer was washed sequentially with 0.2 M HCl, 0.5 M NaOH (2×) and brine. Then dried and concentrated. The product was isolated as a yellow solid (112 mg, 100% yield) and was used without further purification.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. customAfter this time, the mixture was quenched by addition of 0.2 M HCl
  3. customThe layers were separated
  4. washthe organic layer was washed sequentially with 0.2 M HCl, 0.5 M NaOH (2×) and brine
  5. customThen dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-276dd41c462e489cbeb6f354863da179
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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