Hydrochloric Acid → HCID 60209036, compound

HRID 239619Notes

Reaction equation

HRID 239619 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:7]=1.[C:19](OC(=O)CC)(=O)[CH2:20][CH3:21].Cl>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][C:19]([CH2:20][CH3:21])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[C:8]2=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 60209035HCID 60209035, compound

Product 1

HCID 60209036HCID 60209036, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 33 (3.0 g, 9.70 mmoles) was taken in a RB flask and to this triethylamine (30 ml) and propionic anhydride (3.94 g, 30.37 mmoles) were added and the mixture was refluxed for 24 h. After cooling to RT, the reaction mixture was acidified by the addition of 1N HCl solution, extracted with ethyl acetate, washed with sodium bicarbonate solution, dried with sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as off-white solid (1.30 g, 39% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 6 8.10(d, J=2.3 Hz, 1H), 7.99(dd, J=8.9,2.4 Hz, 1H), 7.69(d, J=8.9 Hz, 1H), 7.51(q, J=7.9 Hz, 1H), 7.25(dt, J=10.8,2.4 Hz, 1H), 7.15(t, J=12.2 Hz, 2H), 2.57(q, J=7.6 Hz, 2H), 1.20(t, J=7.5 Hz, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 24 h
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-9755e753e01f421c91e8b54b6f749dbf
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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