(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 2213531Notes

Reaction equation

HRID 2213531 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.CNCC1[S:32][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=CN=1.Cl.CN(C)CC[CH2:45][N:46]=[C:47]=[N:48][CH2:49][CH3:50]>CN(C)C=O>[NH2:39][S:36]([C:33]1[S:32][C:47]([N:46]([CH3:45])[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:48][C:49]=1[CH3:50])(=[O:38])=[O:37]

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 219574382-Methylaminomethyl-1,3-thiazole-5-sulphonamide

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

At room temperature, 300 mg (1.41 mmol) of [4-(2-pyridinyl)phenyl]acetic acid and 190 mg (1.41 mmol) of 1-hydroxy-1H-benzotriazole hydrate are initially charged in 4 ml of dimethylformamide. 307 mg (1.48 mmol) of 2-methylaminomethyl-1,3-thiazole-5-sulphonamide 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 under reduced pressure, the residue is taken up in toluene and the solvent is once more removed under reduced pressure. The residue is stirred with 15 ml of water and 3 ml of methanol and then filtered off, and the filtrate is re-extracted with 20 ml of dichloromethane. Solid and dichloromethane phase are combined and the solvent is removed under reduced pressure. This gives the compound of Example 38 in the form of a white solid.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customthe solvent is once more removed under reduced pressure
  3. stirringThe residue is stirred with 15 ml of water and 3 ml of methanol
  4. filtrationfiltered off
  5. extractionthe filtrate is re-extracted with 20 ml of dichloromethane
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-ce644d5f3b5447a7b4773f9c93dffb3c
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

Loading…