Potassium Carbonate → HCID 56654485, compound

HRID 1464969Notes

Reaction equation

HRID 1464969 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])[N:14]=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].[N:22]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:32])[C:26]=2[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:18]([O:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][O:32][C:27]3[CH:28]=[CH:29][CH:30]=[C:31]4[C:26]=3[CH:25]=[CH:24][CH:23]=[N:22]4)[CH2:6][CH2:7]2)[CH:16]=1)[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66748176HCID 66748176, compoundHCID 135441757Quinolin-5-ol

Product 1

HCID 56654485HCID 56654485, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-1-(4-(6-isobutoxypyrimidin-4-yl)piperazin-1-yl)ethanone (20 mg, 0.064 mmol), quinolin-5-ol (10.2 mg, 0.070 mmol), and potassium carbonate (18 mg, 0.13 mmol) in DMF was (0.5 mL) was stirred at 90° C. for 3 h. After cooling to rt, the mixture was poured onto water, and the aqueous later was extracted with dichloromethane (three times). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 9.3 mg (34% yields) of the title compound.

Workup

  1. temperatureAfter cooling to rt
  2. additionthe mixture was poured onto water
  3. extractionthe aqueous later was extracted with dichloromethane (three times)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative LC-MS
  7. customto give

Sources & evidence

ORD record
ord-52fcf364209d4fffa845f8fa8aaa34c1
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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