Water → N-{4-[5-chloro-7-(ethylsulfanyl)-2-(4-fluorophenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-2-pyrimidinyl}-N-phenylamine

HRID 8511

반응식

HRID 8511 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]=3)=[C:4]2[CH:3]=1.C([Li])CCC.[CH2:36]([S:38]SCC)[CH3:37].O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([S:38][CH2:36][CH3:37])[N:5]2[N:8]=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]=3)=[C:4]2[CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8077Diethyl disulfideHCID 112470274-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamineHCID 178418339Butyllithium

생성물 1

HCID 10299224N-{4-[5-chloro-7-(ethylsulfanyl)-2-(4-fluorophenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-2-pyrimidinyl}-N-phenylamine수율 22.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine (80 mg, 0.19 mmol) in tetrahydrofuran (5 mL) was added n-butyllithium (0.43 mL of 1.6M solution in hexane, 0.67 mmol) at −78° C. The resulting dark solution was stirred for 10 minutes, then quenched by the addition of ethyl disulfide (0.08 mL 6.5 mmol). The reaction mixture was allowed to warm to room temperature, then water and ethyl acetate were added. The phases were separated and the ethyl acetate phase was washed with water, dried (magnesium sulfate), filtered and concentrated. The resulting residue was crystallized from acetonitrile to give N-{4-[5-chloro-7-(ethylsulfanyl)-2-(4fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}-N-phenylamine (20 mg, 22%) as a solid. 1H NMR (CDCl3): δ 8.30 (d, 1H), 8.22 (d, 1H), 7.66 (m, 3H), 7.40 (t, 2H), 7.1–7.24 (m, 4H), 6.75 (d, 1H), 6.52 (d, 1 H), 3.20 (q, 2H), 1.54 (t, 3H); 19F-NMR (CDCl3): δ −112.55; MS m/z 476 (M+1).

후처리

  1. customThe phases were separated
  2. washthe ethyl acetate phase was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was crystallized from acetonitrile

출처 및 근거

ORD 기록
ord-56267b581f904460a878984962e92f00
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087618B2

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