Hydrochloric Acid → 3-Amino-5-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]isothiazole-4-carboxamide

HRID 871031Notes

Reaction equation

HRID 871031 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[F:26])=[O:17])=[CH:11][CH:10]=2)[S:4][N:3]=1.Cl.CC[O:30]C(C)=O>CCO.[OH-].[Na+].OO>[NH2:1][C:2]1[C:6]([C:7]([NH2:8])=[O:30])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=3[F:26])=[O:17])=[CH:11][CH:10]=2)[S:4][N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 866892261-(4-(3-Amino-4-cyanoisothiazol-5-yl)phenyl)-3-(2-fluoro-5-methylphenyl)urea

Product 1

HCID 716230283-Amino-5-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]isothiazole-4-carboxamideYield 93%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 1-[4-(3-amino-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea (10.2 mg, 0.028 mmol) in 0.8 mL EtOH at rt was added 15 drops 1.0M aqueous NaOH, 7 drops 30% hydrogen peroxide and the reaction stirred at rt for 30 min, then heated at 60° C. After 2.5 hours an aqueous HCl (dilute) and EtOAc workup was done to give a light yellow solid. To this material was added an impure lot from another reaction, and the combined lots triturated with EtOAc to give the title compound as a pale yellow solid (26 mg, 93% combined yield).

Workup

  1. temperatureheated at 60° C
  2. customto give a light yellow solid
  3. additionTo this material was added an impure lot
  4. customfrom another reaction
  5. customthe combined lots triturated with EtOAc

Sources & evidence

ORD record
ord-ec2754825a154ff5a2f8bb4b6ef7725b
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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