Methanesulfonic Acid → HCID 86608139, compound

HRID 228461Notes

Reaction equation

HRID 228461 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:27]=[CH:26][C:15]([O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=3)=[C:14]([O:28][CH3:29])[CH:13]=2)=[CH:4][CH:3]=1.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>ClCCl.CO.ClCCl>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:27]=[CH:26][C:15]([O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=3)=[C:14]([O:28][CH3:29])[CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59730332HCID 59730332, compound

Product 1

HCID 86608139HCID 86608139, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Dissolve 6-(4-{[2-(4-fluorophenyl)ethylamino]methyl}-2-methoxyphenoxy)nicotinamide (Example 430) (8.40 g, 2.12 mmol) in dichloromethane:methanol (1:1) (4.25 mL) and add 1 equivalent of 0.50 M methanesulfonic acid in dichloromethane. Stir the solution for a short time before concentrating to give the title compound (0.1.02 g): TOF MS ES+ 396.2 (M+H)+, HRMS calcd for C22H23N3O3.F 396.1723 (M+H)+, found 396.1731, time 0.39 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=10.9 min, 100% purity.

Workup

  1. concentrationbefore concentrating

Sources & evidence

ORD record
ord-ac6e3c59a1024c028350c57d861eed50
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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