Difluoroacetic acid → HCID 118023989, compound

HRID 2171804Notes

Reaction equation

HRID 2171804 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[F:23][CH:24]([F:28])[C:25](O)=[O:26].[NH2:29][C:30]1[S:31][C:32]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:33][C:34]=1[C:35]([NH2:37])=[O:36]>[Cl-].[Na+].O.CN(C=O)C>[CH:38]1([C:32]2[S:31][C:30]([NH:29][C:25](=[O:26])[CH:24]([F:28])[F:23])=[C:34]([C:35]([NH2:37])=[O:36])[CH:33]=2)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

7

Reactant 4

HCID 9788Difluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 80400357HCID 80400357, compound

Product 1

HCID 118023989HCID 118023989, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of WSC hydrochloride (4.5 g), HOBt (3.2 g), and DMF (50 mL) were added difluoroacetic acid (2 mL) and 2-amino-5-cyclohexylthiophene-3-carboxamide (5.0 g), followed by stirring at room temperature for 3 days. To the reaction mixture was added 50% brine, followed by extraction with EtOAc. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate, water, and brine. To the organic layer were added MgSO4, and basic silica gel was added thereto, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain 5-cyclohexyl-2-[(difluoroacetyl)amino]thiophene-3-carboxamide (7.0 g).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate, water, and brine
  3. additionTo the organic layer were added MgSO4, and basic silica gel
  4. additionwas added
  5. stirringby stirring
  6. filtrationThe mixture was filtered through Celite
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9fcdeb9eada5434faedd4d052cce0541
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

Loading…