Carbonic acid-guanidine (1:1) → HCID 86695822, compound

HRID 338698Notes

Reaction equation

HRID 338698 reaction equation
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])[CH:13]=2)[CH2:6]1)C.C(=O)(O)O.[NH2:35][C:36]([NH2:38])=[NH:37].O.O.O.C([O-])(=O)C.[Na+]>CCO>[NH2:37][C:36]1[N:38]=[CH:4][C:5]2[CH2:6][N:7]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=4)=[O:19])[CH:13]=3)[CH2:8][CH2:9][C:10]=2[N:35]=1

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 86695823HCID 86695823, compound

Product 1

HCID 86695822HCID 86695822, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-[3-(dimethylamino)methylidene-4-oxopiperidin-1-yl]-N-[3-(trifluoromethyl)phenyl]pyridine-2-carboxamide (417 mg, 0.997 mmol) in EtOH (10 ml) was treated with guanidine carbonate (719 mg, 3.99 mmol), followed by adding sodium acetate trihydrate (1.09 g, 7.98 mmol). The reaction mixture was stirred at 80° C. for 23 hours and concentrated. The residue was partitioned between EtOAc and water resulting in the formation of a yellow, amorphous solid. The solid was collected, washed with water, EtOAc, MeOH, and dried to give the title compound (59 mg, 14%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc and water resulting in the formation of a yellow, amorphous solid
  3. customThe solid was collected
  4. washwashed with water, EtOAc, MeOH
  5. customdried

Sources & evidence

ORD record
ord-1a6bcf73ab8a4c2f90d843fc26d0f53d
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

Loading…