Barbituric Acid → HCID 70901148, compound

HRID 245563Notes

Reaction equation

HRID 245563 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[C:21]([CH:22]=O)=[CH:20][C:11]3[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][O:14][C:10]=3[C:9]=2[F:24])[CH2:5][C@H:4]([CH3:25])[O:3]1.[NH:26]1[C:33](=[O:34])[CH2:32][C:30](=[O:31])[NH:29][C:27]1=[O:28]>C(O)C>[F:24][C:9]1[C:10]2[O:14][N:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]=2[CH:20]=[C:21]2[C:8]=1[N:6]1[CH2:5][C@@H:4]([CH3:25])[O:3][C@@H:2]([CH3:1])[C@@H:7]1[C:32]1([C:30](=[O:31])[NH:29][C:27](=[O:28])[NH:26][C:33]1=[O:34])[CH2:22]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 86658115HCID 86658115, compound2×

Product 1

HCID 70901148HCID 70901148, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-5-formylbenzo[d]isoxazole-3-carboxylate (Intermediate 439, 350 mg, 1.00 mmol) and barbituric acid (141 mg, 1.10 mmol) were heated to reflux in ethanol (45 ml) for 64 hours. The reaction was concentrated. The residue was dissolved in DCM, absorbed onto silica and purified by silica gel column chromatography using a gradient of DCM to ethyl acetate, to give the title compound (412 mg, 76%) as a racemic mixture.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was dissolved in DCM
  3. customabsorbed onto silica
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-eaed4b07f4c94cecaa46e17b2193d396
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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