Ethanol → N-(7-propargyloxy-1,8-naphthyridin-2-yl)-4-methoxybenzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][CH2:24][C:25]#[CH:26])=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[CH2:24]([O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1)[C:25]#[CH:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (11.5 g), N,N'-carbonyldiimidazole (12 g) and 2-amino-7-propargyloxy-1,8-naphthyridine (10 g). The product produced by precipitation in water (15.3 g; m.p. 140° C.) is dissolved in boiling ethanol (190 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (3×20 cc) and dried at 50° C. under reduced pressure (0.067 kPa). N-(7-propargyloxy-1,8-naphthyridin-2-yl)-4-methoxybenzamide (10.1 g) is produced, m.p. 140° C.
Workup
- dissolutionis dissolved
- customthe crystallised solid is separated by filtration
- washwashed with ethanol (3×20 cc)
- customdried at 50° C. under reduced pressure (0.067 kPa)
Sources & evidence
- ORD record
- ord-a8e06522851f4bc198a52a45cdce1096
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04642308
Reaction notes
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