Methyl iodide → HCID 70654872, compound

HRID 2091587Notes

Reaction equation

HRID 2091587 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][C:6]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH:29][C@@H:30]3[CH2:32][C@H:31]3[CH3:33])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[N:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH2:13][CH2:12]2.[C:34](=O)([O-])[O-].[Cs+].[Cs+].CI>>[NH2:2][C:3]1[N:4]=[CH:5][C:6]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([N:29]([CH3:34])[C@@H:30]3[CH2:32][C@H:31]3[CH3:33])(=[O:27])=[O:28])=[CH:24][CH:25]=2)=[N:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH2:13][CH2:12]2

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70654828HCID 70654828, compound

Product 1

HCID 70654872HCID 70654872, compoundYield 86%

Procedure

To a room temperature slurry of 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-((1R,2R)-2-methylcyclopropyl)benzenesulfonamide hydrochloride (110 mg, 0.227 mmol) and cesium carbonate (222 mg, 0.681 mmol) was added methyl iodide (16.0 μL, 0.251 mmol). At completion, the reaction was filtered and concentrated, then flashed over silica gel (5-10% MeOH/DCM eluent) to provide 4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)-N-methyl-N-((1R,2R)-2-methylcyclopropyl)-benzenesulfonamide (90 mg, 86% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.55 (s, 1H), 8.25 (d, J=7.8 Hz, 1H), 8.16 (d, J=8.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 7.83 (dd, J=8.0, 1.5 Hz, 1H), 7.70 (s, 1H), 5.95 (br. s, 1H), 5.14 (br. s, 2H), 3.66 (dt, J=7.0, 2.3 Hz, 2H), 3.14 (t, J=7.0 Hz, 2H), 2.76 (s, 3H), 1.48-1.53 (m, 1H), 1.27-1.35 (m, 1H), 1.06 (d, J=6.3 Hz, 3H), 0.96-1.02 (m, 1H), 0.47 (dd, J=12.3, 6.0 Hz, 1H); MS (EI) m/z=464.5 [M+1]+.

Workup

  1. filtrationAt completion, the reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b322b84d5dbf4d38a85bf8a524c8e51d
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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