Benzamide → Ispinesib mesylate

HRID 1373369Notes

Reaction equation

HRID 1373369 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C@@H:15]([C:19]1[N:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](=[O:36])[C:26]2[C:21](=[CH:22][C:23]([Cl:37])=[CH:24][CH:25]=2)[N:20]=1)[CH:16]([CH3:18])[CH3:17])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.C(N)(=O)C1C=CC=CC=1.[CH3:47][S:48]([OH:51])(=[O:50])=[O:49]>CC(OC)(C)C>[S:48]([OH:51])(=[O:50])(=[O:49])[CH3:47].[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([C@@H:15]([C:19]1[N:28]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:27](=[O:36])[C:26]2[C:21](=[CH:22][C:23]([Cl:37])=[CH:24][CH:25]=2)[N:20]=1)[CH:16]([CH3:17])[CH3:18])[C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 2331BenzamideHCID 6395Methanesulfonic AcidHCID 6851740Ispinesib

Product 1

HCID 6450816Ispinesib mesylateYield 86%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
10 °C

Procedure

A dry round bottomed flask, equipped with a magnetic stirrer, dropping funnel, cooling bath and nitrogen bubbler was charged with 10 g (1 eq.) of (R)-N-(3-amino-propyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-4-methyl-benzamide and 50 mL of MTBE, and stirred until the benzamide was dissolved. The solution was cooled to 10° C. and slowly charged with 1.86 g (1 eq.) of methane sulfonic acid via the dropping funnel. When the addition was complete, the solution was warmed to room temperature and quickly charged with 50 mL of hexanes. The resulting solid was isolated by filtration under Nitrogen, washed with 100 mL of hexanes, and dried under vacuum at 60° C. to constant weight affording the title salt of Formula I, (R)-N-(3-amino-propyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-4-methyl-benzamide, mesylate salt (10.2 g, 86% yield).

Workup

  1. customA dry round bottomed flask, equipped with a magnetic stirrer
  2. temperaturecooling bath
  3. dissolutionwas dissolved
  4. additionWhen the addition
  5. temperaturethe solution was warmed to room temperature
  6. customThe resulting solid was isolated by filtration under Nitrogen
  7. washwashed with 100 mL of hexanes
  8. customdried under vacuum at 60° C. to constant weight

Sources & evidence

ORD record
ord-09baedcb65fc41f2b2fe7f82b89e1427
Source dataset
uspto-grants-2007_01
Patent number
US07161002B2

Reaction notes

Loading…