Methanesulfonic Acid → HCID 86713647, compound

HRID 1257209Notes

Reaction equation

HRID 1257209 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][C:33]([F:36])=[CH:32][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][C:33]([F:36])=[CH:32][CH:31]=2)=[O:28])=[C:4]([F:37])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584955HCID 71584955, compound

Product 1

HCID 86713647HCID 86713647, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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-(4-fluorophenyl)urea, (0.220 g, 0.417 mmol) in MeCN (10 mL) was treated with methanesulfonic acid (0.044 g, 0.458 mmol) and stirred at RT for 20 h. The solids were filtered, washed and dried to provide 1-(4-chloro-5-(1-ethyl-7-(2-methoxyethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(4-fluorophenyl)urea methanesulfonate (212 mg, 74% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.16 (s, 1H), 8.75 (s, 1H), 8.54 (s, 1H), 8.28 (b s, 1H), 8.19 (d, J=9 Hz, 1H), 7.89 (s, 1H), 7.58 (d, J=11 Hz, 1H), 7.43 (m, 2H), 7.10 (m, 2H), 6.74 (s, 1H), 4.14 (m, 2H), 3.56 (m, 4H), 3.30 (s, 3H), 2.34 (s, 3H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 528.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-d3a8e523585a4c3191c2cde38a32460b
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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