Potassium Carbonate → HCID 68536542, compound

HRID 1816951Notes

Reaction equation

HRID 1816951 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]([NH:20][C@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[CH3:22])=[O:19])[N:16]=[C:12]3[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][CH2:39][CH2:40]Br>CC(=O)CC.C(Cl)Cl>[CH3:37][O:38][CH2:39][CH2:40][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]([NH:20][C@H:21]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[CH3:22])=[O:19])[N:16]=[C:12]3[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 136330237HCID 136330237, compound2×

Product 1

HCID 68536542HCID 68536542, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-1-[7-(4-hydroxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-3-[1-(3-methoxyphenyl)ethyl]urea (the compound obtained in Example 223; 20.3 mg) was suspended in 2-butanone (2 ml). Thereafter, potassium carbonate (69.4 mg) and 2-methoxyethyl bromide (47.2 μl) were added to the suspension, and the obtained mixture was stirred at 80° C. for 5 hours. Thereafter, the reaction solution was diluted with methylene chloride (5 ml), and the resultant product was then washed with 1 M hydrochloric acid (5 ml×3), saturated sodium bicarbonate (5 ml×2), and distilled water (5 ml×2). The organic layer was concentrated under a reduced pressure, and the obtained residue was purified by reverse phase liquid chromatography (Inertsil PREP-ODS; 20 Φ×250 mm; eluted with water-containing acetonitrile) to obtain the captioned compound (10.7 mg).

Workup

  1. washthe resultant product was then washed with 1 M hydrochloric acid (5 ml×3), saturated sodium bicarbonate (5 ml×2)
  2. distillationdistilled water (5 ml×2)
  3. concentrationThe organic layer was concentrated under a reduced pressure
  4. customthe obtained residue was purified by reverse phase liquid chromatography (Inertsil PREP-ODS
  5. washeluted with water-
  6. additioncontaining acetonitrile)

Sources & evidence

ORD record
ord-a690222e2d2c410b98e461ef1cb60b30
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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