Methanesulfonic Acid → HCID 86713649, compound

HRID 1257211Notes

Reaction equation

HRID 1257211 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]([F: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]([F:35])=[CH:20][C:21]([F:34])=[C:22]([NH:24][C:25]([NH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH:23]=2)[C:4]1=[O:36])[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584958HCID 71584958, compound

Product 1

HCID 86713649HCID 86713649, compoundYield 80%

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)-2,4-difluorophenyl)-3-phenylurea (0.200 g, 0.405 mmol) in MeCN (10 mL) was added methanesulfonic acid (0.039 g, 0.405 mmol) and the mixture stirred at RT for 1 h. The solvent was evaporated and the residue crystallized from MeCN to provide 1-(5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-phenylurea methanesulfonate (190 mg, 80% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.22 (s, 1H), 9.10 (s, 1H), 8.64 (s, 1H), 8.56 (s, 1H), 8.15 (t, J=8 Hz, 1H), 8.00 (s, 1H), 7.42 (m, 3H), 7.26 (m, 2H), 6.96 (t, J=7 Hz, 1H), 6.73 (s, 1H), 4.14 (m, 2H), 3.56 (m, 4H), 3.30 (s, 3H), 2.35 (s, 3H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 494.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-e1ed15b04f7f4d68ba2f4969e5b7ef5f
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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