Hydrochloric Acid → 4-{[({4-(Aminocarbonyl)-3-[4-({[(4-methylphenyl)amino]carbonyl}amino)phenyl]isothiazol-5-yl}amino)carbonyl]amino}butanoic acid

HRID 871010Notes

Reaction equation

HRID 871010 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:22]([C:23]([NH2:25])=[O:24])=[C:21]([NH:26][C:27]([N:29]4[CH2:33][CH2:32][CH2:31][C:30]4=[O:34])=[O:28])[S:20][N:19]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.Cl.[OH-:36].[Na+]>>[NH2:25][C:23]([C:22]1[C:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:10])=[CH:13][CH:14]=2)=[N:19][S:20][C:21]=1[NH:26][C:27]([NH:29][CH2:33][CH2:32][CH2:31][C:30]([OH:34])=[O:36])=[O:28])=[O:24]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 716216293-[4-({[(4-Methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

Product 1

HCID 866892284-{[({4-(Aminocarbonyl)-3-[4-({[(4-methylphenyl)amino]carbonyl}amino)phenyl]isothiazol-5-yl}amino)carbonyl]amino}butanoic acid

Procedure

3-[4-({[(4-methylphenyl)amino]carbonyl}amino)phenyl]-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide (11.8 g,) was added to 1 N sodium hydroxide (100 mL) at ambient temperature. The resulting mixture was stirred at ambient temperature for overnight (reaction mixture became clear solution). Reaction mixture acidified with 2 N HCl. The solid which formed was collected by filtration and washed with water then dried in vacuo to give the title compound as off white solid (9.1 g, 75%).

Workup

  1. custom(reaction mixture became clear solution)
  2. customReaction mixture
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-38faf31f64f740be88c0ef555bfa4064
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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