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

HRID 1161282Notes

Reaction equation

HRID 1161282 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]([CH:19]3[CH2:21][CH2:20]3)[C:14]=2[NH2:18])[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2].[F:23][C:24]1[CH:25]=[C:26]([CH2:34][C:35](O)=[O:36])[CH:27]=[CH:28][C:29]=1[C:30]([F:33])([F:32])[F:31].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][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:19]3[CH2:20][CH2:21]3)[C:14]=2[NH:18][C:35](=[O:36])[CH2:34][C:26]2[CH:27]=[CH:28][C:29]([C:30]([F:31])([F:32])[F:33])=[C:24]([F:23])[CH:25]=2)[C:9]1=[O:22])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 27375913-Fluoro-4-(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 59515874(R)-2-(5-Amino-6-cyclopropyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 59515703(R)-2-(6-Cyclopropyl-5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Conditions

Temperature
40 °C

Procedure

A reaction vial was charged with (R)-2-(5-amino-6-cyclopropyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (23.0 mg, 0.0000766 mol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (26 mg, 0.00011 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (73 mg, 0.00019 mol), N,N-diisopropylethylamine (33 μL, 0.00019 mol) and methylene chloride (2 mL, 0.03 mol) and the reaction stirred at 40° C. over night. The solvent was removed and the residue purified by flash chromatography (0-70% ethylacetate) to obtain the product as light yellow solid. MS m/z=505.3 (M+H).

Workup

  1. customA reaction
  2. customThe solvent was removed
  3. customthe residue purified by flash chromatography (0-70% ethylacetate)

Sources & evidence

ORD record
ord-09ac9f57efbb414c902ee2a1540ba009
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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