Methanesulfonic Acid → HCID 86608136, compound

HRID 228330Notes

Reaction equation

HRID 228330 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([CH2:19][NH:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>C1COCC1.CO>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH3:1][O:2][C:3]1[CH:18]=[C:17]([CH2:19][NH:20][CH2:21][CH2:22][CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:16]=[CH:15][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 597301416-(2-Methoxy-4-{[2-(tetrahydropyran-4-yl)ethylamino]methyl}phenoxy)nicotinamide

Product 1

HCID 86608136HCID 86608136, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 6-(2-methoxy-4-{[2-(tetrahydropyran-4-yl)ethylamino]methyl}phenoxy)nicotinamide (Example 427) (0.612, 1.59 mmol) in THF (4 mL) and few drops of methanol to form a clear solution. Add 1.27 M methanesulfonic acid (1.25 mL, 1.59 mmol) in THF. Stir for 10 minutes, then concentrate to give the title compound (0.749 g, 100%): TOF MS ES+ 386.2 (M+H)+, HRMS calcd for C21H25N3O4 386.2080 (M+H)+, found 386.2083, time 0.62 min; HPLC [Waters XTerra™ MS C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 15 min], tR=6.6 min, 100% purity.

Workup

  1. customto form a clear solution
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-fce25268335a41f880daeab6474a69fb
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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