Hydrochloric Acid → 6-Amino-5-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-phenylethynyl}-nicotinic acid

HRID 1099699Notes

Reaction equation

HRID 1099699 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=3)=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[K+].Cl>CO.O.[Cl-].[Na+].O>[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=3)=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57657963methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate

Product 1

HCID 576578676-Amino-5-{3-[(2,5-dimethyl-2H-pyrazole-3-carbonyl)-amino]-phenylethynyl}-nicotinic acidYield 84%

Reagents, catalysts & solvents 2

HCID 22242641Methanol--water (1/1)SolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate (51 mg, 0.13 mmol) and KOH (37 mg, 0.65 mmol) in 4.0 ml MeOH:H2O (3:1) was heated at 65° C. for 1 hour 40 minutes. The pH of the mixture was adjusted to pH 4 using 10% HCl, brine added, and the aqueous extracted with EtOAc. The combined EtOAc layers were dried with anhydrous Na2SO4 and rotary evaporated. The light yellow solid was triturated with hot EtOAc to give the title compound as an off-white solid (41 mg, 84%).

Workup

  1. additionadded
  2. extractionthe aqueous extracted with EtOAc
  3. dry with materialThe combined EtOAc layers were dried with anhydrous Na2SO4 and rotary evaporated
  4. customThe light yellow solid was triturated with hot EtOAc

Sources & evidence

ORD record
ord-5835e6d6b24c43ec8f02215d4cfba04c
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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