Hydrochloric Acid → (S)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(6-methyl-1-oxo-2-(pyrrolidin-3-yl)-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 418521Notes

Reaction equation

HRID 418521 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]([C@H:28]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]2)[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(Cl)Cl.Cl>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([NH:15][C:16]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]([C@H:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[C:21]3=[O:27])=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 66649399(S)-tert-Butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57990499(S)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(6-methyl-1-oxo-2-(pyrrolidin-3-yl)-1,2-dihydroisoquinolin-5-yl)acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
45 °C

Procedure

A round bottom flask was charged with (S)-tert-butyl 3-(5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate (100.0 mg, 0.0001826 mol), methylene chloride (3 mL, 0.05 mol) and 2M hydrochloric acid in ether (4 mL) was added and the reaction was stirred at 45° C. for 3 hours. The solvent was removed under reduced pressure under reduced pressure and the residue was purified by reverse phase preparative HPLC to afford the product as white solid.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure under reduced pressure
  3. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-5905ab8104e846c1b23069afb1235b56
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

Loading…