3-Fluoro-4-(methylsulfonyl)phenol → 4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester

HRID 1931633Notes

Reaction equation

HRID 1931633 reaction equation
FC1C=C(S(C)(=O)=O)C=CC=1OC1N=CN=C2N(C3CCC(C4ON=C(C(C)C)N=4)CC3)N=CC=12.[CH:36]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([N:48]2[C:52]3=[N:53][CH:54]=[N:55][C:56](Cl)=[C:51]3[CH:50]=[N:49]2)[CH2:44][CH2:43]1)=[O:41])([CH3:38])[CH3:37].[F:58][C:59]1[CH:60]=[C:61]([OH:69])[CH:62]=[CH:63][C:64]=1[S:65]([CH3:68])(=[O:67])=[O:66]>CN(C)C=O>[CH:36]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([N:48]2[C:52]3=[N:53][CH:54]=[N:55][C:56]([O:69][C:61]4[CH:62]=[CH:63][C:64]([S:65]([CH3:68])(=[O:67])=[O:66])=[C:59]([F:58])[CH:60]=4)=[C:51]3[CH:50]=[N:49]2)[CH2:44][CH2:43]1)=[O:41])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 231456203-Fluoro-4-(methylsulfonyl)phenol2×HCID 44514990HCID 44514990, compoundHCID 575444174-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester2×

Product 1

HCID 579649334-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester was prepared using the procedure described above 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 129) by the reaction of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester (Intermediate 20) 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-[4-(3-fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester (70 mg, 40%) as a white solid. Mass spectrum (ES) MH+=478.

Workup

  1. custom4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester was prepared
  2. customThe product was purified by flash chromatography
  3. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-486d4007038d4e41ba0f1ea0005490f2
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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