Methanesulfonic Acid → Taprizosin mesylate

HRID 1840761Notes

Reaction equation

HRID 1840761 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([O:18][CH3:19])[C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:5]=[C:4]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]2)[N:3]=1.[CH3:37][S:38]([OH:41])(=[O:40])=[O:39]>CC(C)=O.O>[S:38]([OH:41])(=[O:40])(=[O:39])[CH3:37].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:20][CH3:21])=[C:9]([O:18][CH3:19])[C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:5]=[C:4]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]2)[N:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 6433102Taprizosin

Product 1

HCID 9830194Taprizosin mesylateYield 96%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A suspension of Form E 4-amino-6,7-dimethoxy-2-(5-methanesulfonamido-1,2,3,4-tetrahydro-2-isoquinolyl)-5-(2-pyridyl)quinazoline (1.0 g, 1.97 mmol) in acetone/water (12/7 by volume, 9.5 ml) was heated to reflux. Methanesulfonic acid (0.19 g, 1.99 mmol) was added in one portion. The addition vessel was washed with water (1 ml) and the resulting solution left to cool to room temperature overnight. The solid from the resulting suspension was collected by filtration and dried overnight in vacuo at 45° C. to afford the title compound (1.14 g) as a white solid.

Workup

  1. temperaturewas heated to reflux
  2. washThe addition vessel was washed with water (1 ml)
  3. waitthe resulting solution left
  4. filtrationThe solid from the resulting suspension was collected by filtration
  5. customdried overnight in vacuo at 45° C.

Sources & evidence

ORD record
ord-733fc2b508284401b15c945c7c98f495
Source dataset
uspto-grants-2004_01
Patent number
US06683085B2

Reaction notes

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