Hydrochloric Acid → {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetic acid

HRID 391601Notes

Reaction equation

HRID 391601 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([O:23]C)=[O:22])[CH:17]=[CH:18][CH:19]=2)([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]2[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=2)=[O:35])[CH:28]=1.[OH-].[Na+].Cl>CO.O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([C:14]2[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]2[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=2)=[O:35])[CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57657942methyl {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate

Product 1

HCID 57657920{3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetic acidYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl {3-[N-({6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]phenyl}acetate (13 mg, 0.021 mmol) and 1.0M NaOH (0.171 ml, 0.171 mmol) in 2.0 ml MeOH and 0.1 ml H2O was stirred at room temperature for 1 hour 10 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 washed with brine, dried with anhydrous Na2SO4 and rotary evaporated. The white solid was triturated with hot EtOAc to give white solid (11 mg, 92%).

Workup

  1. additionadded
  2. extractionthe aqueous extracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe white solid was triturated with hot EtOAc

Sources & evidence

ORD record
ord-9aae40e1590740d391c334a59fc1ab47
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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