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

HRID 2201072

Reaction equation

HRID 2201072 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].[NH2:12][C@H:13]([CH2:17][CH:18]1[CH2:20][CH2:19]1)[C:14]([NH2:16])=[O:15].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:12][C@H:13]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:14]([NH2:16])=[O:15])[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 192612772-Bromo-4,5-difluorobenzonitrileHCID 59001002(R)-2-amino-3-cyclopropylpropanamide

Product 1

HCID 67508107(R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-cyclopropylpropanamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4,5-difluorobenzonitrile (218 mg, 1.00 mmol), (R)-2-amino-3-cyclopropylpropanamide (188 mg, 1.14 mmol) and DIEA (0.600 mL, 3.45 mmol) in DMSO (3 mL) was stirred at 120 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo to give (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-cyclopropylpropanamide (326 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c434196f0eb473ca1c2169d53ac448e
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Linked notes

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