Water → 1-(2-Fluoro-4-methanesulfonyl-phenyl)-4-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-1H-pyrazolo[3,4-d]pyrimidine

HRID 719467

Reaction equation

HRID 719467 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]2[N:25]([C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][C:29]=3[F:38])[N:26]=[CH:27][C:20]=12.O>C1COCC1>[F:38][C:29]1[CH:30]=[C:31]([S:34]([CH3:37])(=[O:35])=[O:36])[CH:32]=[CH:33][C:28]=1[N:25]1[C:21]2=[N:22][CH:23]=[N:24][C:19]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:14][CH2:13]3)=[C:20]2[CH:27]=[N:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 218976614-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Product 1

HCID 218978311-(2-Fluoro-4-methanesulfonyl-phenyl)-4-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-ol (338 mg, 1.6 mmol) and sodium hydride (87 mg, 3.66 mmol) were stirred together in dry THF (2 mL) at room temperature for 30 minutes. 4-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine was then added and the reaction continued to stir at room temperature for 45 minutes. Its progress was monitored by thin layer chromatography and LCMS. The reaction was treated with water and the desired compound was extracted with ethyl acetate. Organic layer was evaporated in vacuo. Purification by HPLC provided the desired Compound A198 as a white solid (600 mg, 98%). Exact mass calculated for C22H24FN7O4S 501.53, found 502.2 (MH+).

Workup

  1. extractionthe desired compound was extracted with ethyl acetate
  2. customOrganic layer was evaporated in vacuo
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-72693c33d2ad4afaad578e55bd8b3c5d
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Linked notes

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