Reaction equation
[CH:1]([N:4]([CH:8]=[N:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[OH:16])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].CO>CCOCC.C(Cl)Cl>[CH3:24][N:25]([CH3:29])[C:26]([O:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[N:9]=[CH:8][N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:2])[CH3:3])=[O:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred mixture of 4-[[(diisopropylamino)methylene]amino]-3-pyridinol (1.06 g) and triethylamine (1.0 ml) in 25 ml dry Et2O was added dimethyl carbamyl chloride (0.53 ml). The mixture was stirred at room temperature for 2 hours, after which no starting material remained as seen by TLC (silica, 10:90 CH3OH:CH2Cl2). The mixture was diluted with 25 ml Et2O, filtered, washed with Et2O, and the filtrate concentrated in vacuo and chromatography on silica using EtOAc eluent. The fractions containing desired product were combined and concentrated to provide 500 mg of pure product. Another run was carried out in the same manner as above using 740 mg of starting material. The products from both runs were combined. Recrystallization attempts failed, and the product was dried in vacuo to provide 790 mg of a white solid, m.p. 76°-79° C.
Workup
- filtrationfiltered
- washwashed with Et2O
- concentrationthe filtrate concentrated in vacuo and chromatography on silica
- additionThe fractions containing desired product
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55b4507bc77f454c88f27ac3dfb2534f
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869480
Linked notes
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