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Triethylamine → [6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine

HRID 1452623
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HRID 1452623 반응식
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6](Cl)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1.C(N(CC)CC)C.[CH3:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>C(O)(C)C>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH3:23])=[CH:27][CH:28]=2)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 90764-EthoxyanilineHCID 575268493-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol

생성물 1

HCID 57526854[6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine수율 67.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
40 °C

실험 절차

To an isopropanol (3 mL) solution containing 3-(5,7-dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol (224 mg, 0.910 mmol), triethylamine (253 μL, 1.82 mmol) and phenethidine (128 μL, 1.00 mmol) were added, and this mixture was stirred at 40° C. for 5 hr. After the reaction, the solvent was distilled off, aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated and the residue was purified with column chromatography (30% ethyl acetate-hexane) to obtain the title compound (212 mg).

후처리

  1. additionwere added
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionaqueous sodium hydrogen carbonate was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified with column chromatography (30% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-c62276d5338a481cb80cd81436d76fe6
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07473694B2

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