Methanesulfonic Acid → HCID 86713655, compound

HRID 1257218Notes

Reaction equation

HRID 1257218 reaction equation
[Br: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]=[CH:32][CH:31]=2)=[O:28])=[C:4]([F:36])[CH:3]=1.[CH3:37][S:38]([OH:41])(=[O:40])=[O:39]>CC#N>[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].[Br: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]=[CH:32][CH:31]=2)=[O:28])=[C:4]([F:36])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71585047HCID 71585047, compound

Product 1

HCID 86713655HCID 86713655, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(4-bromo-5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (0.200 g, 0.361 mmol) in MeCN (4 mL) was added methanesulfonic acid (0.035 g, 0.361 mmol) and the mixture was stirred at RT for 30 minutes. The solvent was completely evaporated and the residue was crystallized from MeCN to provide 1-(4-bromo-5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea methanesulfonate (0.160 g, 67% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.23 (s, 1H), 9.04 (s, 1H), 8.53 (s, 1H), 8.22 (d, J=9 Hz, 2H), 7.87 (s, 1H), 7.70 (d, J=11 Hz, 1H), 7.41 (d, J=9 Hz, 2H), 7.26 (t, J=7 Hz, 2H), 6.96 (t, J=7 Hz, 1H), 6.72 (s, 1H), 4.13 (m, 2H), 3.56 (m, 4H), 3.30 (s, 3H), 2.33 (s, 3H), 1.21 (d, J=6 Hz, 3H); MS (ESI) m/z: 554.1/556.1 [M+H]+.

Workup

  1. customThe solvent was completely evaporated
  2. customthe residue was crystallized from MeCN

Sources & evidence

ORD record
ord-7d73ee9d3bcb4af7ad241540cd58c0c6
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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