Dichloromethane → HCID 68533774, compound

HRID 1816953Notes

Reaction equation

HRID 1816953 reaction equation
[CH3:1][C@H:2]([NH:9][C:10]([NH:12][C:13]1[N:28]=[C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[N:15]2[N:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[CH3:35][O:36][CH2:37][CH2:38]Br.C(Cl)Cl>C(C(C)=O)C>[CH3:1][C@H:2]([NH:9][C:10]([NH:12][C:13]1[N:28]=[C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:38][CH2:37][O:36][CH3:35])=[CH:25][CH:26]=3)[N:15]2[N:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 135507469HCID 135507469, compound2×

Product 1

HCID 68533774HCID 68533774, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-1-(1,5-dimethylhexyl)-3-[7-(4-hydroxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]urea (the compound obtained in Example 255; 30 mg) and potassium carbonate (108 mg) were suspended in methyl ethyl ketone (3 ml). Thereafter, 2-methoxyethyl bromide (327 mg) was added to the obtained suspension, and the obtained mixture was stirred at 80° C. for 10 hours. Thereafter, the reaction solution was cooled to a room temperature, and methylene chloride (5 ml) was then added thereto. The obtained mixture was washed with an aqueous 1 M hydrochloric acid solution (5 ml×3), an aqueous saturated sodium bicarbonate solution (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 (14 mg).

Workup

  1. temperatureThereafter, the reaction solution was cooled to a room temperature
  2. washThe obtained mixture was washed with an aqueous 1 M hydrochloric acid solution (5 ml×3)
  3. distillationan aqueous saturated sodium bicarbonate solution (5 ml×2), and distilled water (5 ml×2)
  4. concentrationThe organic layer was concentrated under a reduced pressure
  5. customthe obtained residue was purified by reverse phase liquid chromatography (Inertsil PREP-ODS; 20 Φ×250 mm; eluted with water-containing acetonitrile)

Sources & evidence

ORD record
ord-52210bee98b647a6ad6f938c48bc90e9
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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