Potassium Carbonate → 2-{5-[(Cyclopropylamino)carbonyl]-2-methylphenyl}-1-oxo-1,2-dihydroisoquinolin-7-yl trifluoromethanesulfonate

HRID 506977Notes

Reaction equation

HRID 506977 reaction equation
[CH:1]1([NH:4][C:5](=[O:25])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([OH:23])=[CH:18][CH:19]=4)[C:14]3=[O:24])[CH:7]=2)[CH2:3][CH2:2]1.C1(N[S:33]([C:36]([F:39])([F:38])[F:37])(=[O:35])=[O:34])C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C(OCC)(=O)C>[F:37][C:36]([F:39])([F:38])[S:33]([O:23][C:17]1[CH:16]=[C:15]2[C:20]([CH:21]=[CH:22][N:13]([C:8]3[CH:7]=[C:6]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:25])[CH:11]=[CH:10][C:9]=3[CH3:12])[C:14]2=[O:24])=[CH:19][CH:18]=1)(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 11515516N-Cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Product 1

HCID 866208532-{5-[(Cyclopropylamino)carbonyl]-2-methylphenyl}-1-oxo-1,2-dihydroisoquinolin-7-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

N-Cyclopropyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (250 mg), N-phenyltrifluoromethanesulfonamide (267 mg) and potassium carbonate (311 mg) were stirred in THF (6 ml) and heated under microwave irradiation (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 120° C. for 10 minutes. The reaction mixture was diluted with ethyl acetate and washed with water (2×), brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography with a gradient of iso-hexane to 70% ethyl acetate/iso-hexane yielded 2-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-oxo-1,2-dihydroisoquinolin-7-yl trifluoromethanesulfonate as a cream coloured solid (264 mg); NMR Spectrum: (DMSOd6) 0.53 (m, 2H), 0.67 (m, 2H), 2.10 (s, 3H), 2.83 (m, 1H), 6.87 (d, 1H), 7.49 (m, 2H), 7.76 (s, 1H), 7.86 (d, 1H), 7.93 (d, 1H), 8.00 (d, 1H), 8.19 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+Na+ 489.

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. customPurification by column chromatography with a gradient of iso-hexane to 70% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-4d186c21753446d691284aa853d7d74d
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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