1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[4-(2,5-difluorophenyl)phenyl]-N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)acetamide

HRID 2213533Notes

Reaction equation

HRID 2213533 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:30][NH:31][C:32]1[S:33][C:34]([S:38]([NH2:41])(=[O:40])=[O:39])=[C:35]([CH3:37])[N:36]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:41][S:38]([C:34]1[S:33][C:32]([N:31]([CH3:30])[C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:3]3[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=3[F:1])=[CH:14][CH:13]=2)=[N:36][C:35]=1[CH3:37])(=[O:39])=[O:40]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112757814-Methyl-2-(methylamino)-1,3-thiazole-5-sulfonamideHCID 219574372',5'-Difluoro-biphenyl-4-acetic acid

Product 1

HCID 5043032-[4-(2,5-difluorophenyl)phenyl]-N-methyl-N-(4-methyl-5-sulfamoyl-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 1.00 g (4.0 mmol) of (2′,5′-difluoro[1,1′-biphenyl]-4-yl)acetic acid and 0.54 g (4.0 mmol) of 1-hydroxy-1H-benzotriazole hydrate are initially charged in 15 ml of dimethylformamide. 0.84 g (4.0 mmol) of 2-methylamino-4-methyl-1,3-thiazole-5-sulphonamide and 0.77 g (4.0 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride are added, and the mixture is stirred at room temperature for 18 h. Most of the dimethylformamide is removed at 50° C. under high vacuum, and the residue is stirred 3 times with in each case 50 ml of water and filtered off, stirred with 50 ml of isopropanol and filtered off once more. Removal of the solvent under reduced pressure gives the compound of Example 87 in the form of a slightly yellow solid.

Workup

  1. customMost of the dimethylformamide is removed at 50° C. under high vacuum
  2. stirringthe residue is stirred 3 times with in each case 50 ml of water
  3. filtrationfiltered off
  4. stirringstirred with 50 ml of isopropanol
  5. filtrationfiltered off once more
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-789ff15475964c03ba9cbb06b8e37dab
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

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