Hydrogen chloride-ethyl acetate → HCID 131729107, compound

HRID 1672852Notes

Reaction equation

HRID 1672852 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[O:33][C:34](=[O:38])[N:35]([CH3:37])[N:36]=2)[CH:27]=1)[C:15]([C:17]1[C:18]([Cl:25])=[N:19][C:20]([CH3:24])=[N:21][C:22]=1[Cl:23])=[S:16])=O)(C)(C)C.Cl.C(OCC)(=O)C>>[ClH:23].[Cl:23][C:22]1[C:17]([C:15]([N:14]([CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]3[O:33][C:34](=[O:38])[N:35]([CH3:37])[N:36]=3)[CH:27]=2)=[S:16])=[C:18]([Cl:25])[N:19]=[C:20]([CH3:24])[N:21]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86643707HCID 86643707, compound

Product 1

HCID 131729107HCID 131729107, compoundYield 159.7%

Procedure

To (S)—N-(1-tert-butoxycarbonyl-pyrrolidin-2-ylmethyl)-4,6-dichloro-N-[3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]-2-methylthiopyrimidine-5-carboxamide (1.30 g, 2.18 mmol) obtained in Step 6 was added 4 mol/L hydrochloric acid-ethyl acetate (11 mL), and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, and the residue was crystallized from hexane and ethyl acetate. The resulting solid was filtered and dried. This procedure was repeated to give (S)-4,6-dichloro-N-(pyrrolidin-2-ylmethyl)-N-[3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]-2-methylthiopyrimidine-5-carboxamidehydrochloride (898 mg, 77%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from hexane and ethyl acetate
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-3bd90a089c3341dab4dd26a07ec2c351
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…