Barbituric Acid → HCID 58457183, compound

HRID 578021Notes

Reaction equation

HRID 578021 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][C@H:12]([CH3:14])[O:11][C@H:10]([CH3:15])[CH2:9]2)=[C:6]([CH:16]=O)[N:5]=[C:4]2[C:18]([C:21]3[S:25][C:24]([CH3:26])=[N:23][CH:22]=3)=[N:19][O:20][C:3]=12.[NH:27]1[C:34](=[O:35])[CH2:33][C:31](=[O:32])[NH:30][C:28]1=[O:29]>C(O)(C)C>[Cl:1][C:2]1[C:3]2[O:20][N:19]=[C:18]([C:21]3[S:25][C:24]([CH3:26])=[N:23][CH:22]=3)[C:4]=2[N:5]=[C:6]2[C:7]=1[N:8]1[CH2:9][C@@H:10]([CH3:15])[O:11][C@@H:12]([CH3:14])[C@@H:13]1[C:33]1([C:31](=[O:32])[NH:30][C:28](=[O:29])[NH:27][C:34]1=[O:35])[CH2:16]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 87369240HCID 87369240, compound2×

Product 1

HCID 58457183HCID 58457183, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To isopropanol (20 ml) was added to 7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(2-methylthiazol-5-yl)isoxazolo[4,5-b]pyridine-5-carbaldehyde (Intermediate 414, 0.26 g, 0.66 mmol) and barbituric acid (0.085 g, 0.66 mmol), and the mixture was heated to 80° C. for about 2 days. The mixture was concentrated, and crystallization of the crude mixture from methanol gave 45 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customcrystallization of the crude mixture from methanol

Sources & evidence

ORD record
ord-12e124ecad5a497fb9601f15966a7a66
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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