Water → (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide

HRID 84852Notes

Reaction equation

HRID 84852 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:13][C@H:14]([CH2:18][O:19][CH3:20])[C:15]([NH2:17])=[O:16].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[C:3]([C:4]#[N:5])=[CH:6][C:7]([F:11])=[C:8]([NH:13][C@H:14]([CH2:18][O:19][CH3:20])[C:15]([NH2:17])=[O:16])[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 192612772-Bromo-4,5-difluorobenzonitrileHCID 86666156(R)-2-amino-3-methoxypropanamide hydrochloride

Product 1

HCID 67508869(R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamideYield 21.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4,5-difluorobenzonitrile (168 mg, 0.770 mmol), (R)-2-amino-3-methoxypropanamide hydrochloride (120 mg, 0.776 mmol) and DIEA (0.500 mL, 2.87 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 0-70% EtOAc in hexane to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-methoxypropanamide (52 mg).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column, which
  5. washwas eluted with 0-70% EtOAc in hexane

Sources & evidence

ORD record
ord-23dd50fad26047ad9ff9f271e7b546e0
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

Loading…