Diisopropylethylamine → (R)-2-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1161276Notes

Reaction equation

HRID 1161276 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[C:14]=2[NH2:18])[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][C:23]=1[C:32]([F:35])([F:34])[F:33].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:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[C:14]=2[NH:18][C:29](=[O:30])[CH2:28][C:25]2[CH:26]=[CH:27][C:22]([F:21])=[C:23]([C:32]([F:33])([F:35])[F:34])[CH:24]=2)[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 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 59515650(R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515708(R)-2-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Conditions

Temperature
50 °C

Procedure

A reaction vial was charged with (R)-2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate (210 mg, 0.00071 mol), 2-(4-fluoro-3-(trifluoromethyl)phenyl)acetic acid (300 mg, 0.001 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (600 mg, 0.002 mol), N,N-diisopropylethylamine (600 μL, 0.003 mol) and the reaction was stirred at 50° C. for 5 days. At this point, the reaction was only 50% complete. The solvent was removed and the residue purified by flash chromatography to obtain the product as a light yellow oil. MS m/z=499.3 (M+H).

Workup

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

Sources & evidence

ORD record
ord-e339b131341d4b7fa63f17a10b2cf2ac
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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