Ethyl bromoacetate → HCID 45486797, compound

HRID 429312Notes

Reaction equation

HRID 429312 reaction equation
[C:1]1([NH:11][C:12]([N:14]2[CH2:19][CH2:18][NH:17][C@H:16]([C@@H:20]([NH:22][C:23]3[N:28]=[C:27]([N:29]4[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=5[N:31]=[CH:30]4)[CH:26]=[CH:25][N:24]=3)[CH3:21])[CH2:15]2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>CC(C)=O.O>[CH2:49]([O:48][C:46]([CH2:45][N:17]1[CH2:18][CH2:19][N:14]([C:12](=[O:13])[NH:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH2:15][C@H:16]1[C@@H:20]([NH:22][C:23]1[N:28]=[C:27]([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[CH:30]2)[CH:26]=[CH:25][N:24]=1)[CH3:21])=[O:47])[CH3:50]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 20703610HCID 20703610, compound

Product 1

HCID 45486797HCID 45486797, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[1-(4-(N-naphth-1-yl-carbamoyl)-piperazin-2-yl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 36, Step C; 26 mg) in 0.5 mL of acetone was added potassium carbonate (11 mg) and ethyl bromoacetate (13.2 mg). The solution was stirred for 48 hours at room temperature, then diluted with 0.5 mL of water and extracted with 3×0.5 mL of CH2Cl2. The combined organics were washed with 1 mL of brine, dried with Na2SO4, and concentrated. The residue was purified by preparative HPLC (60:40 95% H2O-5% TFA:95% CH3CN-5% TFA) followed by preparative thin-layer chromatography, eluting with 95:5 25 CHCl3-isopropanol to provide 8.7 mg of the title compound. Mass spectrum (ESI) 579.3 (M+1).

Workup

  1. extractionextracted with 3×0.5 mL of CH2Cl2
  2. washThe combined organics were washed with 1 mL of brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (60:40 95% H2O-5% TFA:95% CH3CN-5% TFA)
  6. washeluting with 95:5 25 CHCl3-isopropanol

Sources & evidence

ORD record
ord-9943d8d1c2424a23ae2d0a916203acc3
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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