Hydrochloric Acid → HCID 9902129, compound

HRID 1374712Notes

Reaction equation

HRID 1374712 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([N:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:8]=1)#[N:2].Cl.[OH-:26].[Na+]>CCOCC>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:10]2[C:11]([C:12]3[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=3)=[C:6]3[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:26])=[CH:8][N:7]3[N:9]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9922847HCID 9922847, compound

Product 1

HCID 9902129HCID 9902129, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-cyano-2-(4-fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridine (Example 52. 100 mg, 0.318 mmol) and concentrated hydrochloric acid (2 mL) were stirred at room temperature overnight. The mixture was diluted with ether, basified with 5N sodium hydroxide solution and extracted thoroughly with ethyl acetate several times. The combined organic layers were dried (MgSO4), filtered and evaporated to dryness. The title compound was isolated in 85% yield (90 mg). 1H NMR (d6-DMSO) δ 9.36 (s, 1H), 8.60 (d, 2H, J=5.2 Hz), 8.22 (bs, 1H), 7.81 (bs, 2H), 7.67 (bs, 1H), 7.58 (m, 2H), 7.28–7.37 (m, 4H). MS (ES+ve): 334 (25, M+2), 333 (100, M+1).

Workup

  1. extractionextracted thoroughly with ethyl acetate several times
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e1c4d2ef5e88437fadbeb90a25b6d42d
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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