3-Fluoro-4-(methylsulfonyl)phenol → 4-(3-fluoro-4-methanesulfonyl-phenoxy)-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine

HRID 1931733Notes

Reaction equation

HRID 1931733 reaction equation
FC1C=C(S(C)(=O)=O)C=CC=1O[C:5]1N=C[N:8]=[C:7]2[N:11](C3CCC(C4ON=C(C(C)C)N=4)CC3)N=[CH:13][C:6]=12.C(O[C:41]([N:43]1[CH2:48][CH2:47][CH:46]([N:49]2[C:53]3=[N:54][CH:55]=[N:56][C:57](Cl)=[C:52]3[CH:51]=[N:50]2)[CH2:45][CH2:44]1)=[O:42])(C)(C)C.[F:59][C:60]1[CH:61]=[C:62]([OH:70])[CH:63]=[CH:64][C:65]=1[S:66]([CH3:69])(=[O:68])=[O:67]>CN(C)C=O>[F:59][C:60]1[CH:61]=[C:62]([CH:63]=[CH:64][C:65]=1[S:66]([CH3:69])(=[O:67])=[O:68])[O:70][C:51]1[C:52]2[C:53](=[N:54][CH:55]=[N:56][CH:57]=2)[N:49]([CH:46]2[CH2:45][CH2:44][N:43]([C:41]3[O:42][N:11]=[C:7]([CH:6]([CH3:13])[CH3:5])[N:8]=3)[CH2:48][CH2:47]2)[N:50]=1.[F:59][C:60]1[CH:61]=[C:62]([CH:63]=[CH:64][C:65]=1[S:66]([CH3:69])(=[O:67])=[O:68])[O:70][C:57]1[N:56]=[CH:55][N:54]=[C:53]2[N:49]([CH:46]3[CH2:45][CH2:44][N:43]([C:41]4[O:42][N:11]=[C:7]([CH:6]([CH3:13])[CH3:5])[N:8]=4)[CH2:48][CH2:47]3)[N:50]=[CH:51][C:52]=12

Participants

6

Reactant 3

HCID 231456203-Fluoro-4-(methylsulfonyl)phenol2×HCID 44514990HCID 44514990, compoundHCID 57964905Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate2×

Product 2

HCID 579649374-(3-fluoro-4-methanesulfonyl-phenoxy)-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidineYield 22%HCID 866361103-Fluoro-4-methanesulfonyl-phenoxy-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Fluoro-4-methanesulfonyl-phenoxy-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine was prepared using the procedure described for the preparation of 4-(2-fluoro-4-methanesulfonyl-phenoxy)-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (Example 131) by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19) with 3-fluoro-4-methanesulfonyl-phenol (Intermediate 2) in dimethylformamide. The product was purified by flash chromatography, eluting with 5% methanol/dichloromethane to give 4-(3-fluoro-4-methanesulfonyl-phenoxy)-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (12 mg, 22%) as a white solid. Mass spectrum: Observed 501.9.

Workup

  1. customThe product was purified by flash chromatography
  2. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-541ce21c5a984e219460c538d7cef33c
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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