Ethyl Acetate → 4-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

HRID 861110

반응식

HRID 861110 반응식
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[N:9][N:10]2[C:15]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:14][CH:13]=[CH:12][C:11]=12)=O.S(O)(O)(=O)=O.[NH2:35][C:36]([NH2:38])=[NH:37].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:8]2[C:7]([C:5]3[CH:4]=[CH:3][N:35]=[C:36]([NH2:38])[N:37]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 499987Guanidine Sulfate (1:1)HCID 57494731(2E)-3-(dimethylamino)-1-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one

생성물 1

HCID 574447144-[2-(4-Methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2E)-3-(dimethylamino)-1-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propen-1-one (500 mg, 1.28 mmol) in dimethylformamide (10 mL) was added guanidine sulfate (277 mg, 1.28 mmol), followed by potassium carbonate (195 mg, 1.41 mmol). The resulting solution was heated at reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added. The phases were separated and aqueous phase extracted with additional ethyl acetate. The combined organics were dried (magnesium sulfate), filtered and concentrated in vacuo to give 4-[2-(4-methoxyphenyl)-7-(1-pyrrolidinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (440 mg, 89%) as a yellow solid. 1H NMR (CDCl3): δ 7.98 (d, 1H), 7.80 (d, 1H), 7.56 (dd, 2H), 7.20 (t, 1H), 6.92 (d, 2H), 6.43 (d, 1H), 6.05 (d, 1H), 4.95 (b, 2H), 3.83 (s, 3H), 3.74–3.70 (m, 4H), 2.01–1.98 (m, 4H); MS m/z 387 (M+1).

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 6 hours
  3. customThe phases were separated
  4. extractionaqueous phase extracted with additional ethyl acetate
  5. dry with materialThe combined organics were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c04da291309f4552a0af9eab46c76e32
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153855B2

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