Methanesulfonic Acid → HCID 86713643, compound

HRID 1430493Notes

Reaction equation

HRID 1430493 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:12]=3)=[CH:6][C:5]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[O:28])=[C:4]([F:37])[CH:3]=1.[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]>CC#N>[CH3:38][S:39]([OH:42])(=[O:41])=[O:40].[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:12]=3)=[CH:6][C:5]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[O:28])=[C:4]([F:37])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584927HCID 71584927, compound

Product 1

HCID 86713643HCID 86713643, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(4-chloro-5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-fluorophenyl)urea, (0.300 g, 0.568 mmol) in MeCN (10 mL) was added methanesulfonic acid (0.055 g, 0.568 mmol). After stirring at RT for 1 h, the solvent was completely evaporated and the residue was crystallized from EtOH to provide 1-(4-chloro-5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-fluorophenyl)urea methanesulfonate as a white solid (0.295 g, 83% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.37 (s, 1H), 8.84 (s, 1H), 8.55 (s, 1H), 8.30 (s, 1H), 8.18 (d, J=8 Hz, 1H), 7.91 (s, 1H), 7.59 (d, J=11 Hz, 1H), 7.47 (m, 1H), 7.29 (m, 1H), 7.07 (m, 1H), 6.77 (m, 2H), 4.15 (m, 2H), 3.56 (m, 4H), 3.30 (s, 3H), 2.37 (s, 3H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 528.2 [M+H]+.

Workup

  1. customthe solvent was completely evaporated
  2. customthe residue was crystallized from EtOH

Sources & evidence

ORD record
ord-322dcdc0da7343a58594dbe0e48ef459
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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