Potassium Carbonate → HCID 178440461, compound

HRID 1931737Notes

Reaction equation

HRID 1931737 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]([C@H:23]3[CH2:28][CH2:27][C@H: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]([C@H:23]3[CH2:28][CH2:27][C@H: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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161288422-Fluoro-4-methylsulfonylphenol2×HCID 178440459HCID 178440459, compound2×

Product 1

HCID 178440461HCID 178440461, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-fluoro-4-methanesulfonyl-phenol (Intermediate 1; 93 mg, 0.49 mmol), 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-trans-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 26; 170 mg, 0.49 mmol) and potassium carbonate (81 mg, 0.59 mmol) in anhydrous DMF (5 mL) was heated in a microwave at 180° C. for 10 min. The mixture was filtered. The filtrate was concentrated and purified using a Supelco 23 g column, eluting with 0-3% methanol/dichloromethane to give 4-(2-fluoro-4-methanesulfonyl-phenoxy)-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-trans-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (153 mg, 62%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified
  4. washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-e8acd04babd14af7b86caef2323392ac
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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