Methanesulfonic Acid → HCID 86713650, compound

HRID 1257212Notes

Reaction equation

HRID 1257212 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([NH:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=2)[CH:6]=[C:5]([C:18]2[C:19]([CH3:35])=[CH:20][C:21]([F:34])=[C:22]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])[CH:23]=2)[C:4]1=[O:36])[CH3:2].[CH3:37][S:38]([OH:41])(=[O:40])=[O:39]>CC#N>[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([NH:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=2)[CH:6]=[C:5]([C:18]2[C:19]([CH3:35])=[CH:20][C:21]([F:34])=[C:22]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])[CH:23]=2)[C:4]1=[O:36])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584959HCID 71584959, compound

Product 1

HCID 86713650HCID 86713650, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-phenylurea (0.500 g, 1.021 mmol) in MeCN (10 mL) was added methanesulfonic acid (0.098 g, 1.021 mmol) and the mixture stirred at RT for 1 h. The solids were filtered, washed, and dried to provide 1-(5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-phenylurea methanesulfonate as a white solid (468 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.07 (s, 1H), 8.54 (m, 2H), 8.30 (br s, 1H), 7.98 (d, J=9 Hz, 1H), 7.83 (s, 1H), 7.42 (m, 2H), 7.25 (m, 2H), 7.16 (d, J=12 Hz, 1H), 6.94 (t, J=8 Hz, 1H), 6.77 (s, 1H), 4.18 (m, 2H), 3.60 (m, 4H),3.30 (s, 3H), 2.31 (s, 3H), 2.07 (s, 3H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 490.2 [M+H]+.

Workup

  1. filtrationThe solids were filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-9c2bc701d5434bfea44b0fb769daac16
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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