Ethyl bromoacetate → HCID 25205109, compound

HRID 1803059Notes

Reaction equation

HRID 1803059 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:6][N:5]([S:7]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[S:12][C:11]=2[NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])(=[O:9])=[O:8])[CH2:4]1.C(N(CC)C(C)C)(C)C.Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].CCOC(C)=O>CN(C=O)C>[F:27][C:21]1[CH:22]=[C:23]([I:26])[CH:24]=[CH:25][C:20]=1[NH:19][C:11]1[S:12][C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[C:10]=1[S:7]([N:5]1[CH2:6][CH:3]([CH2:2][NH:1][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:4]1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 25207538HCID 25207538, compound

Product 1

HCID 25205109HCID 25205109, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of Example 2 (200 mg, 0.39 mmol) and N,N-diisopropyl-ethylamine (68 μL, 42 mmol) in DMF (5 mL) was added ethyl bromoacetate (43 μL, 0.39 mmol) and the mixture allowed to stir for 18 hours. After this time EtOAc (25 mL) was added to the reaction mixture which was then washed with brine (3×25 mL), dried (sodium sulfate) and then reduced in vacuo. The resulting oil was purified by column chromatography (SiO2, 50% DCM in EtOAc) to afford the title compound as a white solid (47 mg, 20%). LCMS (pH 3) RT 2.24 minutes, (ES+) 605 (M+H).

Workup

  1. washwas then washed with brine (3×25 mL)
  2. dry with materialdried (sodium sulfate)
  3. customThe resulting oil was purified by column chromatography (SiO2, 50% DCM in EtOAc)

Sources & evidence

ORD record
ord-240450cf29c449dab331eabe530af89c
Source dataset
uspto-grants-2013_01
Patent number
US08350037B2

Reaction notes

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