Barbituric Acid → HCID 70901148, compound

HRID 578024Notes

Reaction equation

HRID 578024 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 refux 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-80db986a8bed45c98e18a55053a60a74
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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