Trifluoroacetic acid → HCID 70872340, compound

HRID 1616452Notes

Reaction equation

HRID 1616452 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]([CH3:49])=[C:16]([N:33]([CH2:47][CH3:48])[CH:34]2[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]2)[CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:22][CH:21]=2)[CH:19]=1)=[O:13].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:22][CH:21]=2)[CH:17]=[C:16]([N:33]([CH2:47][CH3:48])[CH:34]2[CH2:35][CH2:36][NH:37][CH2:38][CH2:39]2)[C:15]=1[CH3:49])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70872705HCID 70872705, compound

Product 1

HCID 70872340HCID 70872340, compoundYield 81.81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-((5-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-4-methyl-4′-(morpholinomethyl)-[1,1′-biphenyl]-3-yl)(ethyl)amino)piperidine-1-carboxylate (1.3 g, 0.1.93 mmol) was taken in DCM (20 mL), to it TFA (10 mL) was added at 0° C. and stirred at rt for 2 h. On completion of reaction, solvent was removed under reduced pressure, reaction was quenched with aqueous sodium bicarbonate and extracted with 10% MeOH/DCM. Combined organic layers were dried over sodium sulphate and concentrated under reduced pressure to obtain crude; which then purified by acetonitrile washing to give the title compound (0.9 g, 81.81%).

Workup

  1. additionwas added at 0° C.
  2. customOn completion of reaction, solvent
  3. customwas removed under reduced pressure, reaction
  4. customwas quenched with aqueous sodium bicarbonate
  5. extractionextracted with 10% MeOH/DCM
  6. dry with materialCombined organic layers were dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain crude
  9. customwhich then purified by acetonitrile washing

Sources & evidence

ORD record
ord-b8143492b15e4d10888d27229559ed51
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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