Water → (R)-2-(3-bromo-4-cyanophenylamino)-3-cyclohexylpropanamide

HRID 84824Notes

Reaction equation

HRID 84824 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C@H:12]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13]([NH2:15])=[O:14].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:9]=[C:8]([NH:11][C@H:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH2:15])=[O:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 445294(R)-2-amino-3-cyclohexylpropanamide

Product 1

HCID 67509667(R)-2-(3-bromo-4-cyanophenylamino)-3-cyclohexylpropanamideYield 63.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), (R)-2-amino-3-cyclohexylpropanamide (280 mg, 1.64 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, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-70% EtOAc in hexane to give (R)-2-(3-bromo-4-cyanophenylamino)-3-cyclohexylpropanamide (222 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 0-70% EtOAc in hexane

Sources & evidence

ORD record
ord-6ddd994d2a3144a28adac0cd99d653ec
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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