Ethyl bromoacetate → HCID 59145191, compound

HRID 2389381Notes

Reaction equation

HRID 2389381 reaction equation
[C:1]([N:9]([CH2:24][CH2:25][CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][CH2:11][NH:12][C:13]([C:15]1[C:16]2[CH2:17][CH2:18][NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.Br[CH2:58][C:59]([O:61][CH2:62][CH3:63])=[O:60]>CN(C=O)C.CCOC(C)=O>[C:1]([N:9]([CH2:24][CH2:25][CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:10][CH2:11][NH:12][C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][N:19]2[CH2:58][C:59]([O:61][CH2:62][CH3:63])=[O:60])=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 68536565HCID 68536565, compound

Product 1

HCID 59145191HCID 59145191, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{2-[benzoyl(3,3-diphenylpropyl)amino]ethyl}-4-indolinecarboxamide (77.0 mg) and 2-(tert-butylimino)-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (106 μL) in DMF (2.3 mL) was added ethyl bromoacetate (39 μL) and the mixture was stirred at ambient temperature for 40 hours. The resulting mixture was diluted with EtOAc (20 mL), washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform: MeOH=99:1) to afford ethyl {4-[({2-[benzoyl(3,3-diphenylpropyl)amino]ethyl}amino)-carbonyl]-2,3-dihydro-1H-indol-1-yl}acetate (87 mg) as an yellow syrup.

Workup

  1. washwashed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform: MeOH=99:1)

Sources & evidence

ORD record
ord-06364e57b4fd40cabf427eb6e7208ba3
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…