Potassium Carbonate → HCID 86667844, compound

HRID 1524303Notes

Reaction equation

HRID 1524303 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:41])[NH:24][C:25]3[S:26][C:27]4[CH2:33][C@@H:32]([NH:34][C:35](=[O:40])[C:36]([F:39])([F:38])[F:37])[CH2:31][CH2:30][C:28]=4[N:29]=3)[CH:18]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].C([O-])([O-])=[O:43].[K+].[K+]>CO.O>[F:37][C:36]([F:39])([F:38])[C:35]([OH:40])=[O:43].[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:41])[NH:24][C:25]3[S:26][C:27]4[CH2:33][C@@H:32]([NH2:34])[CH2:31][CH2:30][C:28]=4[N:29]=3)[CH:18]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86667845HCID 86667845, compound

Product 1

HCID 86667844HCID 86667844, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stifling solution of crude (R)-2-{3-[(S)-6-(2,2,2-trifluoro-acetylamino)-4,5,6,7-tetrahydro-benzothiazol-2-ylcarbamoyl]-phenyl}-pyrrolidine-1-carboxylic acid (3-cyano-phenyl)-amide (87 mg, 0.149 mmol) in MeOH (5 mL) and water (1 mL) at room temperature add anhydrous K2CO3 (200 mg, 1.447 mmol) and stir the reaction at 65° C. for 18 h. Remove the solvent in vacuo and dry the solid residue in vacuo. Suspend in DMF and filter off the K2CO3. Dilute with water and quench with TFA (0.5 mL). Purify the solution by reverse phase prep HPLC (10% to 90% CH3CN/water). Pool and concentrate fractions containing product and dry in vacuo to afford the title compound as a solid (35 mg). MS, electrospray 487.5 (M+H), rt 1.26 min.

Workup

  1. customthe reaction at 65° C. for 18 h
  2. customRemove the solvent in vacuo
  3. customdry the solid residue in vacuo
  4. filtrationfilter off the K2CO3
  5. additionDilute with water
  6. customquench with TFA (0.5 mL)
  7. customPurify the solution by reverse phase prep HPLC (10% to 90% CH3CN/water)
  8. concentrationPool and concentrate fractions
  9. additioncontaining product
  10. customdry in vacuo

Sources & evidence

ORD record
ord-bd90fa0504c245699e91727c17e3e8bd
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

Loading…