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Felbinac → N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)-2-(4-phenylphenyl)acetamide

HRID 2213530
Notes
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Reaction equation

HRID 2213530 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:28][NH:29][C:30]1[S:31][C:32]([S:36]([NH2:39])(=[O:38])=[O:37])=[C:33]([CH3:35])[N:34]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:39][S:36]([C:32]1[S:31][C:30]([N:29]([CH3:28])[C:8](=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][C:1]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:5]=2)=[N:34][C:33]=1[CH3:35])(=[O:37])=[O:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3332FelbinacHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112757814-Methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide

Product 1

HCID 5278580N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)-2-(4-phenylphenyl)acetamide

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

138.2 mg (0.65 mmol) of 4-biphenylacetic acid and 99.7 mg (0.65 mmol) of 1-hydroxy-1H-benzotriazole hydrate are initially charged at room temperature in 5 ml of dimethylformamide. 150 mg (0.72 mmol) of 2-methylamino-4-methyl-1,3-thiazole-5-sulphonamide and 138.7 mg (0.72 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride are added, and the mixture is stirred at room temperature for 72 h. The reaction mixture is then filtered off with suction and the residue is recrystallized from 2-propanol. This gives a white solid.

Workup

  1. filtrationThe reaction mixture is then filtered off with suction
  2. customthe residue is recrystallized from 2-propanol
  3. customThis gives a white solid

Sources & evidence

ORD record
ord-96aa32fd65a2407f8fdea9239f621c0e
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07105553B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes