Methanesulfonic Acid → HCID 86713642, compound

HRID 1430492Notes

Reaction equation

HRID 1430492 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][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].[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][CH:31]=2)=[O:28])=[C:4]([F:36])[CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71584902HCID 71584902, compound

Product 1

HCID 86713642HCID 86713642, compoundYield 76%

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-phenylurea, (0.233 g, 0.457 mmol) in MeCN (10 mL) was treated with methanesulfonic acid (0.044 g, 0.457 mmol). The crystallized 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-phenylurea methanesulfonate as a white solid (0.210 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.13 (s, 1H), 8.70 (s, 1H), 8.54 (s, 1H), 8.22 (d, J=9 Hz, 2H), 7.90 (s, 1H), 7.58 (d, J=12 Hz, 1H), 7.42 (d, J=8 Hz, 2H), 7.26 (t, J=8 Hz 2H) 6.97 (t, J=8.5 Hz, 1H), 6.74 (s, 1H), 4.16 (m, 2H), 3.57 (m, 4H), 3.29 (s, 3H), 2.34 (s, 3H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 510.2.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-0c9e5cff26da417f99c526f885193de6
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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