Methanesulfonic Acid → HCID 86641692, compound

HRID 2060732Notes

Reaction equation

HRID 2060732 reaction equation
[Cl:1][C:2]1[C:3]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:25]=2)=[CH:4][C:5]([F:22])=[C:6]([NH:8][C:9]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:10])[CH:7]=1.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>C1COCC1.C(#N)C.CO>[S:37]([OH:40])(=[O:39])(=[O:38])[CH3:36].[Cl:1][C:2]1[C:3]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:25]=2)=[CH:4][C:5]([F:22])=[C:6]([NH:8][C:9]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:10])[CH:7]=1

Participants

6

Reactant 2

HCID 6395Methanesulfonic AcidHCID 46209113HCID 46209113, compound

Product 1

HCID 86641692HCID 86641692, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(5-Chloro-2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea (0.146 g, 0.293 mmol) was fully dissolved in a mixture of THF (4 ml), acetonitrile (4 mL), and methanol (0.5 mL). Methanesulfonic acid (19 μl, 0.293 mmol) was added, and after stirring for several minutes a precipitate started to form. The mixture was stirred at RT for 5 hours. 1-(5-Chloro-2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)urea mesylate salt was obtained by suction filtration and was washed with acetonitrile (0.148 g, 82% yield). 1H NMR (500 MHz, DMSO-d6): δ 11.33 (s, 1H), 10.97 (s, 1H), 8.59 (m, 2H), 8.46 (d, 1H), 8.26 (s, 1H), 7.74 (d, 1H), 7.65 (s, 1H), 7.36 (m, 2H), 7.17 (m, 3H), 3.92 (s, 3H), 3.77 (s, 2H), 2.33 (s, 3H); MS (ESI) m/z: 498.1 (M+H+).

Workup

  1. customto form
  2. stirringThe mixture was stirred at RT for 5 hours

Sources & evidence

ORD record
ord-8ea570080b694e6785c6f4e3f3de6ed9
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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