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Potassium Carbonate → HCID 44514688, compound

HRID 1931732
Notes
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Reaction equation

HRID 1931732 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].Cl[C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[O:33][N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[N:30]=4)[CH2:25][CH2:24]3)[N:21]=[CH:22][C:15]=12.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([CH:23]3[CH2:24][CH2:25][N:26]([C:29]4[O:33][N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[N:30]=4)[CH2:27][CH2:28]3)[N:21]=[CH:22][C:15]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161288422-Fluoro-4-methylsulfonylphenol2×HCID 579649944-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine2×

Product 1

HCID 44514688HCID 44514688, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-fluoro-4-methanesulfonyl-phenol (Intermediate 1; 20 mg, 0.1 mmol), 4-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 22; 31 mg, 0.09 mmol) and potassium carbonate (14 mg, 0.1 mmol) in DMF (2 mL) was heated in a Biotage Optimizer microwave at 180° C. for 10 min. The mixture was cooled and filtered through Celite, concentrated and held under vacuum. The residue was purified on a silica column (ISCO 4 g) eluting with 0-3% methanol/dichloromethane to give 4-(2-fluoro-4-methanesulfonyl-phenoxy)-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (6 mg, 14%). Mass spectrum (ES) MH+=502.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. customThe residue was purified on a silica column (ISCO 4 g)
  5. washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-1ede35b7122e491cb4149908a5baab44
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188098B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes