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 1362787Notes

Reaction equation

HRID 1362787 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

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 introduced into 15 ml of dimethylformamide at room temperature. 0.84 g (4.0 mmol) of 2-methylamino-4-methyl-1,3-thiazole-5-sulfonamide 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. The dimethylformamide is substantially removed at 50° C. under high vacuum, and the residue is stirred 3 times with 50 ml of water each time, filtered off, stirred with 50 ml of isopropanol and again filtered off. Removal of the solvent in vacuo results in the compound of Example 87 in the form of a pale yellow-colored solid.

Workup

  1. customThe dimethylformamide is substantially removed at 50° C. under high vacuum
  2. stirringthe residue is stirred 3 times with 50 ml of water each time
  3. filtrationfiltered off
  4. stirringstirred with 50 ml of isopropanol
  5. filtrationagain filtered off
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-9ae40de49d624b5b85762a2a9dac6c70
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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