Morpholine → HCID 58382519, compound

HRID 1027506Notes

Reaction equation

HRID 1027506 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:14][C:15]3[N:16]=[C:17]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[N:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[C:20]=3[N:21]=2)=[CH:8][C:7]=1[CH3:34].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:17]2[N:18]=[C:19]([O:22][CH2:23][CH2:24][CH3:25])[C:20]3[N:21]=[C:13]([C:9]4[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[C:7]([CH3:34])[CH:8]=4)[O:14][C:15]=3[N:16]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67175933HCID 67175933, compound

Product 1

HCID 58382519HCID 58382519, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 230 mg of 2-[4-(3-bromo-propoxy)-3,5-dimethyl-phenyl]-5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidine, 74 mg of morpholine and 233 mg of potassium carbonate in 5 ml of dimethylformamide was heated to 60° C. for 3 h. After cooling to room temperature, the solids were removed by filtration. The solvent was distilled off in vacuo and the residue was purified by preparative HPLC to yield 137 mg of the title compound in the form of the 5-(4-chloro-benzyl)-2-[3,5-dimethyl-4-(3-morpholin-4-yl-propoxy)-phenyl]-7-propoxy-oxazolo[5,4-d]pyrimidine trifluoroacetic acid salt.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solids were removed by filtration
  3. distillationThe solvent was distilled off in vacuo
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0f3380800ad14f0c9bbbb5bf14795198
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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