Hydrochloric Acid → HCID 60209050, compound

HRID 1484295Notes

Reaction equation

HRID 1484295 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][C:13]([F:16])=[CH:12][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][C:13]([F:16])=[CH:12][CH:11]=1)[C:8]2=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 53234358HCID 53234358, compound

Product 1

HCID 60209050HCID 60209050, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 6 (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 (1.60 g, 47% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 8.33 (d, J=2.4 Hz, 1H), 7.76 (dd, J=8.8, 2.4 Hz, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.24 (dd, J=5.5, 2.0 Hz, 2H), 7.16 (dt, J=11.4, 2.8 Hz, 2H), 2.61 (q, J=7.6 Hz, 2H), 1.27 (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-e033e043e5454d8697a300528f5d1a8f
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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