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

HRID 1931668Notes

Reaction equation

HRID 1931668 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.[C:36]([O:40][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])([CH3:39])([CH3:38])[CH3:37].[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>[C:36]([O:40][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]([O:70][C:62]4[CH:63]=[CH:64][C:65]([S:66]([CH3:69])(=[O:68])=[O:67])=[C:60]([F:59])[CH:61]=4)=[C:52]3[CH:51]=[N:50]2)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]

Participants

5

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 1

HCID 579649344-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl esterYield 43%

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 tert-butyl ester 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)-cyclo-hexyl]-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 tert-butyl ester (Intermediate 19) with 3-fluoro-4-methanesulfonyl-phenol (Intermediate 2) in dimethylformamide. The product was purified by flash chromatography, eluting with 40% ethyl acetate/hexanes to give 4-[4-(3-fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (75 mg, 43%) as a white solid. Mass spectrum: Observed 491.9.

Workup

  1. custom4-[4-(3-Fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester was prepared
  2. customThe product was purified by flash chromatography
  3. washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-11413fa2696c407aabf0014fd3df6d78
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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