Hydrochloric Acid → 3-(5-Ethoxycarbonyl-4-trifluoromethyl-pyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

HRID 351663Notes

Reaction equation

HRID 351663 reaction equation
Cl.[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([NH2:17])=[NH:16])=[N:7]1.Cl.C[O-].[Na+].C(O[CH:29]=[C:30]([C:36](=O)[C:37]([F:40])([F:39])[F:38])[C:31]([O:33][CH2:34][CH3:35])=[O:32])C>CO>[CH2:34]([O:33][C:31]([C:30]1[C:36]([C:37]([F:38])([F:39])[F:40])=[N:16][C:15]([C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:6]([CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=3[F:2])[N:7]=2)=[N:17][CH:29]=1)=[O:32])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoateHCID 10942334Sodium MethoxideHCID 574158441-((2-Fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridine-3-carboximidamide hydrochloride

Product 1

HCID 227142743-(5-Ethoxycarbonyl-4-trifluoromethyl-pyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 mg of the crude 1-(2-fluorobenzyl)1H-pyrazolo[3,4-b]pyridine-3-carboxamidine hydrochloride (preparable from the amidine 25A by reaction with HCl) are stirred in 30 ml of methanol with 106 mg of sodium methoxide and admixed with 472 mg (1.96 mmol) of ethyl 3-ethoxy-2-trifluoroacetyl-acrylate. The mixture is boiled for 12 hours and the precipitate is then filtered off with suction and washed with ether. This gives 249 mg (27.5% of theory) of crystals.

Workup

  1. filtrationthe precipitate is then filtered off with suction
  2. washwashed with ether

Sources & evidence

ORD record
ord-1f47298c27af49ccaeec79f5f6e4527f
Source dataset
uspto-grants-2004_06
Patent number
US06743798B1

Reaction notes

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