Dimethylformamide → HCID 178469972, 화합물

HRID 1026904노트

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HRID 1026904 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([OH:15])=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2].S(Cl)(Cl)=O.[CH3:23]N(C=O)C.C(N(CC)CC)C>ClCCCl.CO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([OH:15])=[C:13]([C:16]([O:18][CH3:23])=[O:17])[CH:12]=[N:11][C:10]=12)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 178469973HCID 178469973, 화합물

생성물 1

HCID 178469972HCID 178469972, 화합물수율 95%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 887Methanol용매

실험 절차

3-Ethoxycarbonyl-7-hydroxypyrazolo[1,5-a]pyrimidine-6-carboxylic acid (27.0 g, 0.11 mol) obtained in Example 19, step 2 was suspended in 1,2-dichloroethane (320 mL), and thionyl chloride (39 mL, 0.54 mol) was added. DMF (22 mL) was added, and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was suspended in methylene chloride (300 mL), and triethylamine (75 mL, 0.54 mol) was added in an ice bath. Methanol (50 mL) was added dropwise over 30 min, and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was added to 2 mol/L hydrochloric acid containing ice (about 500 mL). The precipitated solid was collected by filtration, and washed with water (50 mL) to give the title compound (27.5 g, 95%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue was added to 2 mol/L hydrochloric acid
  6. additioncontaining ice (about 500 mL)
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with water (50 mL)

출처 및 근거

ORD 기록
ord-e76557fb39c242b0896e3d03319b1be1
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729264B2

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