Barbituric Acid → (2R,4S,4aS)-rel-8-amino-11-fluoro-2,4-dimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

HRID 245546Notes

Reaction equation

HRID 245546 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([CH:20]=O)[C:9]([N:12]3[CH2:17][C@H:16]([CH3:18])[O:15][C@H:14]([CH3:19])[CH2:13]3)=[C:10]([F:11])[C:5]=2[O:4][N:3]=1.[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24]>CC(O)C>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]3[C:9](=[C:10]([F:11])[C:5]=2[O:4][N:3]=1)[N:12]1[CH2:13][C@@H:14]([CH3:19])[O:15][C@@H:16]([CH3:18])[C@@H:17]1[C:28]1([C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22][C:29]1=[O:30])[CH2:20]3

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 866580473-amino-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzisoxazole-5-carbaldehyde2×

Product 1

HCID 45381703(2R,4S,4aS)-rel-8-amino-11-fluoro-2,4-dimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3-amino-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzisoxazole-5-carbaldehyde (Intermediate 8, 100 mg, 0.34 mmol) in IPA was added barbituric acid (48 mg, 0.34 mmol) and the mixture heated at 85° C. for 12 hours. Solvents were evaporated and the residue was purified over neutral alumina using a gradient of methanol in CH2Cl2 to give the title compound as a racemic mixture in the form of a pale yellow solid. Yield: 18 mg, (13%).

Workup

  1. customSolvents were evaporated
  2. customthe residue was purified over neutral alumina using a gradient of methanol in CH2Cl2

Sources & evidence

ORD record
ord-524080e3f68043f3b2db65fef00061af
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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