Acetonitrile → HCID 68582659, compound

HRID 2233999Notes

Reaction equation

HRID 2233999 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:22][C:21](C(O)=O)=[N:20][N:19]=2)[CH2:14][CH2:13]1)=[O:10].C(#N)C>C([O-])(=O)C.[NH4+]>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[S:22][CH:21]=[N:20][N:19]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 68582508HCID 68582508, compound

Product 1

HCID 68582659HCID 68582659, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 517165Ammonium AcetateSolvent

Procedure

5-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3,4-thiadiazole-2-carboxylic acid (Example 223; 0.250 g, 0.60 mmol) was stirred in 10 mM ammonium acetate (pH 8) (15 ml) and acetonitrile (15 ml) overnight. The mixture was concentrated then the residue was stirred in acetonitrile and filtered. The solid was dissolved in DMSO and purified using semi-preparative HPLC (10% ammonium acetate:water/acetonitrile (20:80-95:5)) to give the title compound as a white solid (0.092 g).

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationfiltered
  3. dissolutionThe solid was dissolved in DMSO
  4. custompurified

Sources & evidence

ORD record
ord-b69a3227cbcb428faab537d7b3681e69
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

Loading…