Dimethylformamide → HCID 91479032, compound

HRID 1524871Notes

Reaction equation

HRID 1524871 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5](F)[CH:4]=1)#[N:2].Cl.[CH2:18]([NH2:20])[CH3:19].CN(C=O)C>O>[C:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([NH:20][CH2:18][CH3:19])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11198Ethylamine hydrochlorideHCID 69670509HCID 69670509, compound

Product 1

HCID 91479032HCID 91479032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 140 Part A (0.30 g, 1.36 mmol) and ethylamine hydrochloride (0.22 g, 2.72 mmol) were added together with 5 mL of DMF. The mixture was heated at 50° C. under N2 for 2 h. Water was added, and the mixture was extracted with EtOAc. The EtOAc extract was washed with brine, dried over MgSO4 and concentrated, and the residue was purified by flash chromatography (silica, EtOAc/hexane) to give 50 mg of the desired product. MS: 247.3 (M+1)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (silica, EtOAc/hexane)

Sources & evidence

ORD record
ord-23420be350b549f09a4bb25ca31e6289
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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