4-Biphenylacetic acid, 2'-fluoro- → 2-[4-(2-fluorophenyl)phenyl]-N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)acetamide

HRID 1362786Notes

Reaction equation

HRID 1362786 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:29][NH:30][C:31]1[S:32][C:33]([S:37]([NH2:40])(=[O:39])=[O:38])=[C:34]([CH3:36])[N:35]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:40][S:37]([C:33]1[S:32][C:31]([N:30]([CH3:29])[C:15](=[O:17])[CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:13][CH:12]=2)=[N:35][C:34]=1[CH3:36])(=[O:38])=[O:39]

Participants

6

Reactant 4

HCID 211014-Biphenylacetic acid, 2'-fluoro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112757814-Methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide

Product 1

HCID 5043022-[4-(2-fluorophenyl)phenyl]-N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.33 g (73.3 mmol) of (2′-fluoro[1,1′-biphenyl]-4-yl)acetic acid and 9.9 g (73.3 mmol) of 1-hydroxy-1H-benzotriazole hydrate are introduced into 600 ml of dimethylformamide at room temperature. 16.84 g (81.4 mmol) of 2-methylamino-4-methyl-1,3-thiazole-5-sulfonamide and 15.58 g (81.4 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride are added, and the mixture is stirred at room temperature for 18 h. The dimethylformamide is substantially removed at 50° C. under high vacuum, and the residue is taken up in 400 ml of dichloromethane and then washed with 350 ml of each of water and 10% citric acid solution. Drying over magnesium sulfate and removal of the solvent in vacuo results in the compound of Example 57 in the form of a white solid.

Workup

  1. customThe dimethylformamide is substantially removed at 50° C. under high vacuum
  2. washwashed with 350 ml of each of water and 10% citric acid solution
  3. dry with materialDrying over magnesium sulfate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-97f47a914fde4ab680173c1c35daf271
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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