Ammonia → 6-[(1-Methoxy-2-methylindolizin-3-yl)carbonyl]-2-methylquinazolin-4(3H)-one
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:12]([C:14]2[CH:15]=[CH:16][C:17]3[N:22]=[C:21]([CH3:23])O[C:19](=[O:24])[C:18]=3[CH:25]=2)=[O:13])[N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2.[NH3:27].[OH-].[Na+].Cl>>[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:12]([C:14]2[CH:25]=[C:18]3[C:17](=[CH:16][CH:15]=2)[N:22]=[C:21]([CH3:23])[NH:27][C:19]3=[O:24])=[O:13])[N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2Participants
5
Procedure
0.100 g (0.29 mmol) of 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-methyl-4H-3,1-benzoxazin-4-one in 2 ml of a 20% aqueous ammonia solution are heated for 2 hours at 50° C. and then hydrolysed with 3 ml of 10% aqueous sodium hydroxide solution and brought to 50° C. for 2 hours. The reaction medium is acidified with a 1N aqueous solution of hydrochloric acid, to pH=9. The precipitate obtained is filtered off, rinsed with water and then dried under reduced pressure at 40° C. overnight. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 67 mg of a yellow solid are obtained.
Workup
- customThe precipitate obtained
- filtrationis filtered off
- washrinsed with water
- customdried under reduced pressure at 40° C. overnight
- customThe solid obtained
- customis purified by silica gel column chromatography, elution
Sources & evidence
- ORD record
- ord-fd036793773e428db14a80723e220839
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859544B2
Reaction notes
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