Methanesulfonic Acid → 6-(4-{[2-(2-Fluorophenyl)ethylamino]methyl}-2-methoxyphenoxy)nicotinamide methanesulfonate

HRID 131002Notes

Reaction equation

HRID 131002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=2)=[C:14]([O:28][CH3:29])[CH:13]=1.[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>CO.ClCCl>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[O:22])=[CH:19][N:18]=2)=[C:14]([O:28][CH3:29])[CH:13]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 597301146-(4-{[2-(2-Fluorophenyl)ethylamino)methyl}-2-methoxyphenoxy)nicotinamide

Product 1

HCID 866238086-(4-{[2-(2-Fluorophenyl)ethylamino]methyl}-2-methoxyphenoxy)nicotinamide methanesulfonateYield 150.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 6-(4-{[2-(2-fluorophenyl)ethylamino]methyl}-2-methoxyphenoxy)nicotinamide (Example 431) (0.701, 1.18 mmol) in methanol (4.4 mL) and dichloromethane (4.4 mL). Add 0.5 M methanesulfonic acid (3.54 mL, 1.18 mmol) in dichloromethane. Stir for 10 minutes, then concentrate to give the title compound (0.875 g, ˜100%): TOF MS ES+ 396.2 (M+H)+, HRMS calcd for C22H23N3O3F 396.1723 (M+H)+, found 396.1739, time 0.53 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=10.8 min, 100% purity.

Workup

  1. concentrationconcentrate

Sources & evidence

ORD record
ord-3c419fea8dbb4cada60125345c98b91f
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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