Ethyl Acrylate → HCID 25205108, compound

HRID 1803058Notes

Reaction equation

HRID 1803058 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.[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH:38]=[CH2:39].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][CH2:39][CH2:38][C:37]([O:41][CH2:42][CH3:43])=[O:40])[CH2:4]1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 8821Ethyl AcrylateHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 25207538HCID 25207538, compound

Product 1

HCID 25205108HCID 25205108, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of Example 2 (160 mg, 0.31 mmol) and N,N-diisopropyl-ethylamine (57 μL, 31 mmol) in DMF (5 mL) was added ethyl acrylate (51 μL, 0.31 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 colourless oil (71 mg, 38%). δH (CDCl3) 8.97 (1H, s), 8.30 (1H, dd, J 1.6, 4.7 Hz), 8.12 (1H, dd, J 1.6, 8.2 Hz), 7.51 (2H, m), 7.33 (1H, dd, J 8.7, 8.7 Hz), 7.23 (1H, dd, J 4.7, 8.2 Hz), 4.04 (2H, q, J 7.2 Hz), 3.88 (2H, dd, J 8.0, 8.0 Hz), 3.55 (2H, dd, J 5.6, 8.0 Hz), 2.71 (2H, t, J 6.3 Hz), 2.64 (2H, d, J 7.3 Hz), 2.53 (1H, m), 2.33 (2H, t, J 6.3 Hz), 1.17 (3H, t, J 7.2 Hz). Exchangeable protons were not observed. LCMS (pH 10) RT 3.19 minutes, (ES+) 619 (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-5c9d72d649de4d05a5b331567c591050
Source dataset
uspto-grants-2013_01
Patent number
US08350037B2

Reaction notes

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