Barbituric Acid → HCID 58457183, compound

HRID 245560Notes

Reaction equation

HRID 245560 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-7b68667a025b4b1bab05dbbc7861adb7
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

Loading…