Diethyl Ether → N'-{[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-1,3-benzenediamine

HRID 896789

반응식

HRID 896789 반응식
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+].CCOCC>C(O)C>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:32]4[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]5[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 10229829N-cyclopentyl-2-(4-methoxyphenyl)-3-[2-(3-nitroanilino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine

생성물 1

HCID 10141279N'-{[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-1,3-benzenediamine

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

To a solution of N-cyclopentyl-2-(4-methoxyphenyl)-3-[2-(3-nitroanilino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (167 mg, 0.32 mmol) in ethanol (10 mL) was added tin(II)chloride dihydrate (304 mg, 1.60 mmol). The mixture was heated to 75° C. for 8 hours and then cooled to room temperature. Saturated aqueous sodium bicarbonate was added followed by ether. The organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate. Filtration and concentration gave a solid residue which was purified by flash chromatography (1:1 hexanes-ethyl acetate to 100% ethyl acetate) to provide_N′-{4-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-1,3-benzenediamine (40 mg, 25%) as a yellow solid. 1H NMR (CDCl3): δ 8.15 (d, 1 H), 7.82 (d, 1H), 7.64 (d, 2 H), 7.43 (s, 1 H), 7.34 (t, 1 H), 7.15-7.10 (m, 2 H), 7.03 (d, 2 H), 6.86 (d, 1H), 6.55 (d, 1 H), 6.40 (d, 1 H), 6.11-6.06 (m, 2 H), 4.05 (m, 1 H), 3.91 (s, 3 H)<3.69 (broad, 2 H), 2.18 (m, 2 H), 1.90-1.66 (m, 6 H); MS m/z 492 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationFiltration and concentration
  6. customgave a solid residue which
  7. customwas purified by flash chromatography (1:1 hexanes-ethyl acetate to 100% ethyl acetate) to provide_N′-{4-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-1,3-benzenediamine (40 mg, 25%) as a yellow solid

출처 및 근거

ORD 기록
ord-1431ee83d2c644638136e7ab829a8747
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919352B2

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