Guanidine Hydrochloride → HCID 178508872, compound

HRID 1027870Notes

Reaction equation

HRID 1027870 reaction equation
C[O:2][C:3]([CH:5]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[C:6]1=O)=O.Cl.[NH2:19][C:20]([NH2:22])=[NH:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:22][C:20]1[N:21]=[C:3]([OH:2])[C:5]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[C:6]=2[N:19]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 69225494HCID 69225494, compound

Product 1

HCID 178508872HCID 178508872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 20A (1.49 g, 6.4 mmol), guanidine hydrochloride (2.1 g, 22 mmol) and K2CO3 (3.26 g, 24 mmol) in anhydrous DMF (20 mL) was heated at 120° C. for 8 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and partitioned between EtOAc (200 mL) and H2O (150 mL). The aqueous layer was extracted with EtOAc three times. The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to provide a residue. The residue was chromatographed on silica gel eluting with MeOH:EtOAc:CHCl3 (10:45:45) to provide the title compound.

Workup

  1. custompartitioned between EtOAc (200 mL) and H2O (150 mL)
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a residue
  8. customThe residue was chromatographed on silica gel eluting with MeOH:EtOAc:CHCl3 (10:45:45)

Sources & evidence

ORD record
ord-2e53afa629ea47f69d89ca158f18b3d4
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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