Methanesulfonic Acid → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine dimesylate

HRID 49882Notes

Reaction equation

HRID 49882 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:14][N:13]=2)=[CH:9][CH:8]=1>CCOCC>[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:14][N:13]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 151194Vatalanib

Product 1

HCID 865854721-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine dimesylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.583 ml (9 mmol) methanesulfonic acid and, at about 30° C., ether are added to a hot solution of 1.56 g (4.5 mmol) 1-(4-chloroanilino)-4-(4-pyridylmethyl)phthalazine until slight turbidity occurs. As it cools to 0° C., crystals precipitate out; these are filtered off and recrystallized again from methanol. After drying under HV (8 h, 120° C.) and equilibration for 24 h at 20° C. and in room atmosphere, title compound is obtained with a water content of 3.97%; m.p. 145-150° C.; 1H NMR (DMSO-d6) 10.50-11.70 (br), 8.82-8.88 (m, 3H), 8.33-8.39 (m, 1H), 8.18-8.29 (m, 2H), 7.98 (d, 2H), 7.58-7.70 (m, 4H), 4.94 (s, 2H), 2.32 (s, 6H); ESI-MS: (M+H)+=347.

Workup

  1. customcools to 0° C.
  2. customcrystals precipitate out
  3. filtrationthese are filtered off
  4. customrecrystallized again from methanol
  5. customAfter drying under HV (8 h, 120° C.) and equilibration for 24 h at 20° C. and in room atmosphere

Sources & evidence

ORD record
ord-24f6806107174da78e363a9f2ccb1253
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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