Dichloromethane → 2-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

HRID 418513Notes

Reaction equation

HRID 418513 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:18])[C:13]=2[NH2:17])[C:8]1=[O:19])(=[O:3])[CH3:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][C:22]=1[C:31]([F:34])([F:33])[F:32].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:18])[C:13]=2[NH:17][C:28](=[O:29])[CH2:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[C:22]([C:31]([F:32])([F:34])[F:33])[CH:23]=2)[C:8]1=[O:19])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27375934-Fluoro-3-(trifluoromethyl)phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595156762-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Product 1

HCID 595158712-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Conditions

Temperature
45 °C

Procedure

A reaction vial was charged with 2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)ethyl acetate (60.0 mg, 0.000214 mol), 2-(4-fluoro-3-(trifluoromethyl)phenyl)acetic acid (57.0 mg, 0.000256 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (203 mg, 0.000534 mol), N,N-diisopropylethylamine (0.093 mL, 0.00053 mol) and methylene chloride (3 mL, 0.05 mol), and the reaction mixture was stirred at 45° C. for 4 days. The solvent was removed under reduced pressure and the residue was purified by flash chromatography to afford the product as a light yellow solid.

Workup

  1. customA reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-494ad3b39a3547508fe10bdd3f706062
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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