Water → HCID 21897421, compound

HRID 1864160Notes

Reaction equation

HRID 1864160 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([CH2:9][N:10]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11]2)[O:6][N:5]=1)([CH3:3])[CH3:2].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]2[N:23]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][C:27]=3[F:36])[N:24]=[CH:25][C:18]=12.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[F:36][C:27]1[CH:28]=[C:29]([S:32]([CH3:35])(=[O:33])=[O:34])[CH:30]=[CH:31][C:26]=1[N:23]1[C:19]2=[N:20][CH:21]=[N:22][C:17]([NH:15][CH:12]3[CH2:13][CH2:14][N:10]([CH2:9][C:7]4[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[CH2:11]3)=[C:18]2[CH:25]=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 218976614-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidineHCID 574963751-{[3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl]methyl}pyrrolidin-3-amine

Product 1

HCID 21897421HCID 21897421, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(3-isopropyl-[1,2,4]oxadiazol-5-ylmethyl)-pyrrolidin-3-ylamine (354 mg, 1.68 mmol), 4-chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (500 mg, 1.53 mmol), and potassium carbonate (3.18 g, 23 mmol) in THF (20 mL) was refluxed for 2 hours. Water was added to the reaction mixture and the product was extracted with ethylacetate. The ethylacetate layer was dried over MgSO4. The organic layer was concentrated in vacuo to afford compound A133 as a white solid (700 mg, 91%). Exact mass calculated for C22H25FN8O3S 500.18, found 501.1 (MH+).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionthe product was extracted with ethylacetate
  3. dry with materialThe ethylacetate layer was dried over MgSO4
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-290cf50f45514366a17c8b9454154cf8
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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