Diisopropylethylamine → HCID 53530593, compound

HRID 1044038Notes

Reaction equation

HRID 1044038 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].Br[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].CCN(C(C)C)C(C)C>C(#N)C>[CH3:8][NH:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetateHCID 6765263-Amino-N-methylbenzamide

Product 1

HCID 53530593HCID 53530593, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

3-Amino-N-methylbenzamide (371 mg, 2.47 mmol), ethyl 2-bromo-2-phenylacetate (0.29 ml, 1.64 mmol), and DIPEA (0.43 ml, 2.47 mmol) were dissolved in acetonitrile (5 ml) and stirred under microwave irradiation into a sealed vial at 100° C. for 60 minutes (UPLC-MS: complete conversion). Acetonitrile was evaporated, and the crude residue was purified by flash chromatography (DCM/EtOAc=8/2) to obtain ethyl 2-(3-(methylcarbamoyl)phenylamino)-2-phenylacetate (475 mg, 92% yield).

Workup

  1. customAcetonitrile was evaporated
  2. customthe crude residue was purified by flash chromatography (DCM/EtOAc=8/2)

Sources & evidence

ORD record
ord-fcc2cae62fc24786b37518c03889d15b
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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