Barbituric Acid → HCID 67433367, compound

HRID 578023Notes

Reaction equation

HRID 578023 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[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([F:29])[CH:22]=3)=[N:19][O:20][C:3]=12.[NH:30]1[C:37](=[O:38])[CH2:36][C:34](=[O:35])[NH:33][C:31]1=[O:32]>C(O)(C)C>[Cl:1][C:2]1[C:3]2[O:20][N:19]=[C:18]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([F:29])[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:36]1([C:34](=[O:35])[NH:33][C:31](=[O:32])[NH:30][C:37]1=[O:38])[CH2:16]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 87368636HCID 87368636, compound2×

Product 1

HCID 67433367HCID 67433367, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To isopropanol (20 ml) was added to 4-(7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-5-formylisoxazolo[4,5-b]pyridin-3-yl)-2-fluorobenzonitrile (Intermediate 416, 0.126 g, 0.30 mmol) and barbituric acid (0.039 g, 0.30 mmol). The mixture was heated to 80° C. for about 2 days. The mixture was concentrated, and the residue was purified by chromatography on silica using 20% acetone in n-hexane. The solids obtained were triturated with methanol gave 41 mg of product.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by chromatography on silica using 20% acetone in n-hexane
  3. customThe solids obtained
  4. customwere triturated with methanol

Sources & evidence

ORD record
ord-9f2962c9f2404cb0a36594b49d119bd1
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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