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Potassium Carbonate → N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

HRID 1161297
Notes
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Reaction equation

HRID 1161297 reaction equation
C([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:32])[C:13]=2[NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=2)[C:8]1=[O:33])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:32][C:12]1[C:13]([NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:29])([F:30])[F:28])[CH:21]=2)=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:33])[N:7]([CH2:6][CH2:5][OH:4])[CH:16]=[CH:15]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 595158712-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

Product 1

HCID 24760888N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterCatalyst
HCID 887
Methanol
Solvent

Procedure

A round bottom flask was charged with 2-(6-chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate (80.0 mg, 0.000165 mol), potassium carbonate (34.2 mg, 0.000248 mol), methanol and 2 drops of water and the reaction stirred for 20 minutes at room temperature. The reaction was then filtered over sodium sulfate and celite and washed with methanol. The solvent was removed and the residue purified by preparative HPLC (reverse phase) to obtain the product as a pale yellow solid. MS m/z=443.3 (M+H) 1H NMR (400 MHz; DMSO-d6) δ 10.18 (s, 1H), 8.15 (d, J=8.81 Hz, 1H), 7.82 (d, J=6.7 Hz, 1H), 7.77-7.74 (m, 1H), 7.59 (d, J=8.81 Hz, 1H), 7.52 (t, J=9.52 Hz, 1H), 7.46 (d, J=7.40 Hz, 1H), 6.40 (d, J=7.59 Hz, 1H), 4.88 (t, J=5.0 Hz, 1H), 4.00 (t, J=5.55 Hz, 2H), 3.89 (s, 2H), 3.65 (q, J=5.55 Hz, 2H).

Workup

  1. filtrationThe reaction was then filtered over sodium sulfate and celite
  2. washwashed with methanol
  3. customThe solvent was removed
  4. customthe residue purified by preparative HPLC (reverse phase)

Sources & evidence

ORD record
ord-caab95ee7e1a4112bf4cfbea92b5388c
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816371B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes