Ethyl Acetate → HCID 68621753, compound

HRID 2102243Notes

Reaction equation

HRID 2102243 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[N:11]=[C:10]([C:23]3[CH:28]=[C:27](Cl)[CH:26]=[C:25]([Cl:30])[CH:24]=3)[CH:9]=2)=[CH:4][CH:3]=1.ON1C2N=C[CH:39]=[CH:40][C:35]=2N=N1.C([N:44]([CH2:48][CH3:49])C(C)C)(C)C.[ClH:50].[CH3:51]N(C)CCCN=C=NCC.CC[O:64][C:65](C)=[O:66]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:44][CH2:48][CH2:49][C:65]([O:66][C:40]([CH3:39])([CH3:35])[CH3:51])=[O:64])=[O:20])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:23]3[CH:28]=[C:27]([Cl:50])[CH:26]=[C:25]([Cl:30])[CH:24]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67333819HCID 67333819, compound

Product 1

HCID 68621753HCID 68621753, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step E (1.07 g, 2.13 mmol) in DMF (20 mL) was added 1-hydroxy-7-azabenzo-triazole (435 mg, 3.19 mmol), N,N-diisopropylethyl amine (557 μL, 3.19 mmol) β-alanine-t-butyl ester hydrochloride (465 mg, 2.55 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (489 mg, 2.55 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with EtOAc (150 mL), washed with 1N HCl, saturated NaHCO3 solution, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The yellow foam obtained was purified by flash chromatography using 2:5 ethylacetate-hexanes to give the title compound as a white solid. 1H NMR (CDCl3, 500 MHz): δ 7.75 (d, J=1.6 Hz, 2H), 7.73 (d, J=8.2 Hz, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.31 (t, J=1.6 Hz, 1H), 7.18 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.92 (t, J=5.7 Hz, 1H), 6.65 (s, 1H), 5.39 (s, 2H), 3.7 (q, J=5.9 Hz, 2H), 2.57 (t, J=6.1 Hz, 2H), 1.47 (s, 9H). LC-MS: 2.95 min; (M-56)=572.1.

Workup

  1. waitThe reaction was left
  2. washwashed with 1N HCl, saturated NaHCO3 solution, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe yellow foam obtained
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f5b161219bc54be4abd230b745fbfd60
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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