(4-Pyridin-2-YL-phenyl)-acetic acid → N-(5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl)-N-methyl-2-(4-(2-pyridinyl)phenyl)acetamide

HRID 1362785Notes

Reaction equation

HRID 1362785 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=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:14](=[O:16])[CH2:13][C:10]2[CH:9]=[CH:8][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:12][CH:11]=2)=[N:34][C:33]=1[CH3:35])(=[O:37])=[O:38]

Participants

6

Reactant 4

HCID 504301(4-Pyridin-2-YL-phenyl)-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112757814-Methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide

Product 1

HCID 491941N-(5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl)-N-methyl-2-(4-(2-pyridinyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg (1.41 mmol) of [4-(2-pyridyl)phenyl]acetic acid and 190 mg (1.41 mmol) of 1-hydroxy-1H-benzotriazole hydrate are introduced into 4 ml of dimethylformamide at room temperature. 307 mg (1.48 mmol) of 2-methylamino-4-methyl-1,3-thiazole-5-sulfonamide and 284 mg (1.48 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride are added, and the mixture is stirred at room temperature for 18 h. The solvent is then removed in vacuo, the residue is taken up in toluene, and the solvent is again removed in vacuo. The residue is stirred with 15 ml of water and 3 ml of methanol and then filtered off, and the filtrate is back-extracted with 20 ml of dichloromethane. Solid and dichloromethane phase are combined, and the solvent is removed in vacuo. The compound of Example 38 is obtained in the form of a white solid.

Workup

  1. customThe solvent is then removed in vacuo
  2. customthe solvent is again removed in vacuo
  3. stirringThe residue is stirred with 15 ml of water and 3 ml of methanol
  4. filtrationfiltered off
  5. extractionthe filtrate is back-extracted with 20 ml of dichloromethane
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-278f1c45338c4b178713becc70dc56ec
Source dataset
uspto-grants-2011_02
Patent number
US07883713B2

Reaction notes

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