Bromoacetonitrile → HCID 86664830, compound

HRID 1628258Notes

Reaction equation

HRID 1628258 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:3]([NH:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH3:19])[CH:13]=2)[CH:7]=1)=[O:4].Br[CH2:29][C:30]#[N:31].CCN(C(C)C)C(C)C>C(#N)C>[C:30]([CH2:29][NH:1][C@@H:2]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=1)[C:3]([NH:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH3:19])[CH:13]=2)[CH:7]=1)=[O:4])#[N:31]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 67496348HCID 67496348, compound

Product 1

HCID 86664830HCID 86664830, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a rt solution of 23.D (750 mg, 2036 μmol) and bromoacetonitrile (244 mg, 2036 μmol) in acetonitrile was added n,n-diisopropylethylamine (426 μl, 2443 μmol). After stirring at 60° C. for 2 hr, organic solvents were removed under reduced pressure. Purification of the residue by flash chromatography on silica gel using 0-12% MeOH/CH2Cl2 for elution gave the title product 23.E as yellow syrup (706 mg, 85%).

Workup

  1. customorganic solvents were removed under reduced pressure
  2. customPurification of the residue by flash chromatography on silica gel using 0-12% MeOH/CH2Cl2
  3. washfor elution

Sources & evidence

ORD record
ord-4d796b2918a34eba805097114adb00b8
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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