Barbituric Acid → HCID 67431841, compound

HRID 245553Notes

Reaction equation

HRID 245553 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:30]([CH:31]=O)=[CH:29][C:12]3[C:13]([C:16]4[S:17][CH:18]=[C:19]([C:21]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[O:22])[N:20]=4)=[N:14][O:15][C:11]=3[C:10]=2[F:33])[CH2:3]1.[NH:34]1[C:41](=[O:42])[CH2:40][C:38](=[O:39])[NH:37][C:35]1=[O:36]>CC(O)C>[F:33][C:10]1[C:11]2[O:15][N:14]=[C:13]([C:16]3[S:17][CH:18]=[C:19]([C:21]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[O:22])[N:20]=3)[C:12]=2[CH:29]=[C:30]2[C:9]=1[N:4]1[CH2:3][C@@H:2]([CH3:1])[O:7][C@@H:6]([CH3:8])[C@@H:5]1[C:40]1([C:38](=[O:39])[NH:37][C:35](=[O:36])[NH:34][C:41]1=[O:42])[CH2:31]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 87368729HCID 87368729, compound2×

Product 1

HCID 67431841HCID 67431841, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-[4-(morpholin-4-ylcarbonyl)-1,3-thiazol-2-yl]-1,2-benzoxazole-5-carbaldehyde (Intermediate 389, 90 mg, 0.19 mmol) in IPA was added barbituric acid (24 mg, 0.103 mmol) and the mixture heated at 85° C. for 16 hours. Solvents were evaporated and the residue was purified by reverse phase HPLC to give product as solid (as a TFA salt). Yield: 16 mg (14%).

Workup

  1. customSolvents were evaporated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-466c6278400f4669af0422db72dcc3a6
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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