Ethyl bromoacetate → HCID 89610429, compound

HRID 1507710Notes

Reaction equation

HRID 1507710 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CC#N>[CH3:15][N:13]([CH3:14])[C:11](=[O:12])[CH2:10][N:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 586061HCID 586061, compound

Product 1

HCID 89610429HCID 89610429, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-(4-methoxyphenylamino)-N,N-dimethylacetamide (19) (10.7 g, 51.2 mmol) in MeCN (80 mL) and DIPEA (13.4 ml, 77 mmol) was added ethyl bromoacetate (6.84 ml, 61.4 mmol) the reaction was stirred at 60° C. for 16 h. The volatiles were removed in vacuo, and the crude mixture was dissolved in EtOAc (150 mL), washed with 1M HCl (aq.) (150 mL), brine (150 mL), dried (MgSO4), filtered and solvents removed in vacuo to afford a purple oil. The residue was purified by silica gel chromatography (120 g, 60-100% EtOAc in isohexane) to afford ethyl 2-((2-(dimethylamino)-2-oxoethyl)(4-methoxyphenyl)amino)acetate (X) (12.9 g, 85%) as a purple oil: m/z 295.4 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 6.81-6.71 (m, 2H), 6.60-6.47 (m, 2H), 4.24-3.96 (m, 6H), 3.66 (s, 3H), 2.99 (br s, 3H), 2.83 (br s, 3H), 1.19 (t, J=7.1 Hz, 3H).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe crude mixture was dissolved in EtOAc (150 mL)
  3. washwashed with 1M HCl (aq.) (150 mL), brine (150 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvents removed in vacuo
  7. customto afford a purple oil
  8. customThe residue was purified by silica gel chromatography (120 g, 60-100% EtOAc in isohexane)

Sources & evidence

ORD record
ord-46ece891517b483baaab7da82198293f
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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