Sodium Iodide → HCID 9807547, compound

HRID 1354181Notes

Reaction equation

HRID 1354181 reaction equation
Cl[CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:17][N:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=23)=[CH:11][CH:10]=1)(=[O:8])=[O:7])=[O:4].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36].[I-].[Na+]>C1COCC1>[NH3:5].[CH2:35]([N:37]([CH2:38][CH3:39])[CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:17][N:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=23)=[CH:11][CH:10]=1)(=[O:8])=[O:7])=[O:4])[CH3:36]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8021DiethylamineHCID 21104429HCID 21104429, compound

Product 2

HCID 222AmmoniaHCID 9807547HCID 9807547, compoundYield 120.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(2-chloroacetyl)-4-[2-(3-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]benzenesulfonamide (0.1 g 0.2 mmol), diethylamine (0.073 g 1 mmol) and sodium iodide (0.005 g 0.03 mmol) in dry THF (5 ml) was stirred at room temperature for 24 hr. The solvent was removed and the residues partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was dried (MgSO4), the solvent removed and the residues were purified by SPE chromatography using a cartridge containing an ion exchange sorbent that retains amino functionality. Elution with 5% acetic acid in methanol, ethyl acetate then 2M ammonia in methanol gave the title compound as a yellow solid (0.066 g 60%). MH+: 549

Workup

  1. customThe solvent was removed
  2. customthe residues partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed
  5. customthe residues were purified by SPE chromatography
  6. additioncontaining an ion exchange sorbent that
  7. washElution with 5% acetic acid in methanol, ethyl acetate

Sources & evidence

ORD record
ord-cf3d5acca97144ac906c1722a5ee6269
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

Loading…