Sodium Bicarbonate → 3(2H)-Isothiazolone, 2-butyl-5-phenyl-4-[(1,2,3,4-tetrahydro-6-isoquinolinyl)amino]-, 1,1-dioxide

HRID 729323Notes

Reaction equation

HRID 729323 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:6]1(=[O:36])=[O:35])[CH2:2][CH2:3][CH3:4].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][NH:17][CH2:16][CH2:15]3)=[C:7]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[S:6]1(=[O:35])=[O:36])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 11605944HCID 11605944, compound

Product 1

HCID 115967233(2H)-Isothiazolone, 2-butyl-5-phenyl-4-[(1,2,3,4-tetrahydro-6-isoquinolinyl)amino]-, 1,1-dioxideYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl 6-[(2-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]-3,4-dihydroisoquinoline-2(1H)-carboxylate (example 24) (0.585 g, 1.144 mmol) in DCM (10 ml) and TFA (2 ml) was stirred at rt for 2.5 h. The reaction mixture was basified by addition of saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine. The mixture was evaporated and the residue was purified by flash chromatography using 0-20% MeOH in DCM as eluent to give the title compound (0.315 g, 67%). 1H NMR (500 MHz DMSO-d6); δ 9.44 (bs, 1H), 7.26 (td, 1H), 7.19 (td, 2H), 7.05 (d, 2H), 6.76-6.68 (m, 3H), 6.29 (s, 1H), 3.78 (s, 2H), 3.69 (t, 2H), 2.86 (t, 2H), 2.27 (t, 3H), 1.78-1.68 (m, 2H), 1.46-1.36 (m, 2H), 0.93 (t, 3H); 13C NMR (125 MHz CDCl3): 159.5, 134.4, 134.3, 130.7, 129.6, 129.5, 128.3, 126.6, 125.4, 122.9, 119.9, 111.2, 46.9, 43.1, 40.5, 30.5, 28.1, 20.3, 13.8: Mass Spectrum: M+H+ 412.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e2e7f9b1202547c0b6d34de132d87324
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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