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 607445Notes

Reaction equation

HRID 607445 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11]([CH3:41])(=[N:13][C:14]([C:16]2[CH:17]=[N:18][C:19]([NH2:40])=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([C:33]4[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[CH:34]=4)=[O:32])[CH:25]=3)[CH:21]=2)=[O:15])=[O:12])[CH:6]=1.[OH-].[Na+].Cl>CO.O.[Cl-].[Na+].O>[NH2:40][C:19]1[N:18]=[CH:17][C:16]([C:14]([N:13]=[S:11]([C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:42])=[O:2])[CH:10]=[CH:9][CH:8]=2)([CH3:41])=[O:12])=[O:15])=[CH:21][C:20]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([C:33]2[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[CH:34]=2)=[O:32])[CH:25]=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-06dcc1df90324ccd9034d7758b8d3bae
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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