Water → (R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamide

HRID 84893

Reaction equation

HRID 84893 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][C:17]1[S:18][CH:19]=[CH:20][CH:21]=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][C:17]2[S:18][CH:19]=[CH:20][CH:21]=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 67508269(R)-2-amino-3-(thiophen-2-yl)propanamide

Product 1

HCID 67508155(R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamideYield 18.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4-fluorobenzonitrile (120 mg, 0.600 mmol), (R)-2-amino-3-(thiophen-2-yl)propanamide (93 mg, 0.547 mmol) and DIEA (0.200 mL, 1.15 mmol) in DMSO (3 mL) was stirred at 120 C for 4 d. 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 0-80% EtOAc in hexane to give (R)-2-(3-bromo-4-cyanophenylamino)-3-(thiophen-2-yl)propanamide (35 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 0-80% EtOAc in hexane

Sources & evidence

ORD record
ord-a84a8b96db9e4390b0eab2dd9c528572
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Linked notes

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