Sodium hydride → HCID 11340908, compound

HRID 719487Notes

Reaction equation

HRID 719487 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])[CH:7]=[CH:8][CH:9]=1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]2[N:26]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=3)[N:27]=[CH:28][C:21]=12>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]([N:12]2[CH2:13][CH2:14][CH:15]([O:18][C:20]3[N:25]=[CH:24][N:23]=[C:22]4[N:26]([C:29]5[CH:30]=[CH:31][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:33][CH:34]=5)[N:27]=[CH:28][C:21]=34)[CH2:16][CH2:17]2)=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 218974474-Chloro-1-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidineHCID 21897782(3-Fluorophenyl)(4-hydroxypiperidin-1-yl)methanone

Product 1

HCID 11340908HCID 11340908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 16 mL reaction vial was placed sodium hydride (48 mg, 60% in oil, 1.2 mmol) and 5 mL of THF. (3-Fluoro-phenyl)-(4-hydroxy-piperidin-1-yl)-methanone (66 mg, 0.3 mmol) was added to the suspension and the mixture was stirred 60 min under N2 at room temperature, followed by the addition of 4-chloro-1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine (60 mg, 0.2 mmol). After stir another 2 hrs under N2 at room temperature, all of the starting chloropyrozolepyrimidines was completely converted as indicated by LCMS. The reaction mixture was then filtered through a syringe filter and purified HPLC to give Compound A8. 1H NMR (CDCl3,400 MHz) δ 1.95 (m, 2H), 2.21 (m, 2H), 3.11 (s, 3H), 3.45 (m, 1H), 3.68 (m, 1H), 3.75 (m, 1H), 4.20 (s, 1H), 5.72 (m, 1H), 7.12 (m, 1H), 7.16 (m, 1H), 7.22 (m, 1H), 7.41 (m, 1H), 8.11 (d, 2H), 8.27 (s, 1H), 8.62 (d, 2H), 8.67 (s, 1H). Exact mass calculated for C24H22FN5O4S 495.14, found 496.3 (MH+)

Workup

  1. customIn a 16 mL reaction
  2. stirringAfter stir another 2 hrs under N2 at room temperature
  3. filtrationThe reaction mixture was then filtered through a syringe
  4. filtrationfilter
  5. custompurified HPLC

Sources & evidence

ORD record
ord-87eaf2e0438c43278554d87b71fb214b
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Reaction notes

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