Methanesulfonic Acid → HCID 86713648, compound

HRID 1257210Notes

Reaction equation

HRID 1257210 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]=[CH:32][C:31]=2[F:36])=[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]=[CH:32][C:31]=2[F:36])=[O:28])=[C:4]([F:37])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584957HCID 71584957, compound

Product 1

HCID 86713648HCID 86713648, compoundYield 79%

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-(2-fluorophenyl)urea (0.220 g, 0.417 mmol) in MeCN (10 mL) was treated with methanesulfonic acid (0.040 g, 0.417 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-(2-fluorophenyl)urea methanesulfonate (205 mg, 79% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.22 (s, 1H), 9.10 (s, 1H), 8.54 (s, 1H), 8.25 (d, J=9 Hz, 1H), 8.18 (br s, 1H), 8.10 (m, 1H), 7.89 (s, 1H), 7.60 (d, J=11 Hz, 1H), 7.23 (m, 1H), 7.10 (m, 1H), 7.00 (m, 1H), 6.72 (s, 1H), 4.14 (m, 2H), 3.56 (m, 4H), 3.30 (s, 3H), 2.31 (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-7d187a6ef0ea41e2bca0570377870a4e
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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