Diethyl Ether → 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

HRID 861144

반응식

HRID 861144 반응식
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=3)[C:10]([C:11](=O)[C:12]#[CH:13])=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[CH:23]1([NH:28][C:29]([NH2:31])=[NH:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C)C=O.O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=3)[C:10]([C:11]3[CH:12]=[CH:13][N:31]=[C:29]([NH:28][CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[N:30]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 574447371-[7-Chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, 화합물

생성물 1

HCID 865967674-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine수율 45.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-one (4.04 g, 13.0 mmol) in N,N-dimethylformamide (100 mL) was added cyclopentyl guanidine hydrochloride (6.36 g, 39 mmol), followed by solid potassium carbonate (5.39 g, 39 mmol). The resultant solution was heated to reflux for 6 hours. Upon cooling to room temperature, ether was added followed by water. The organics were washed with brine, and the aqueous extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (3:10 ethyl acetate:hexanes) to give 4-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (2.39 g, 43%) as a yellow foam. 1H NMR (CDCl3) δ 8.47 (d, 1H), 7.99 (d, 1H), 7.48 (s, 1H), 7.39 (d, 1H), 7.33–7.24 (m, 3H), 7.05 (d, 1H), 6.33 (d, 1H), 5.38 (broad s, 1H), 4.36 (m, 1H), 2.40 (s, 3H), 2.10 (m, 2H), 1.78 (m, 2H), 1.67 (m, 2H), 1.58 (m, 2H); MS m/z 404 (M+1).

후처리

  1. temperatureto reflux for 6 hours
  2. washThe organics were washed with brine
  3. extractionthe aqueous extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (3:10 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-485d09d83293425fade5f4235992ea36
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153855B2

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