Dimethylformamide → HCID 17838182, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13]([CH:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:18]([OH:20])=O)[CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl.C(N=C=N[CH2:33][CH2:34][CH2:35][N:36](C)C)C.ON1[C:44]2[CH:45]=CC=[CH:48][C:43]=2N=N1.CN(C1C=CC=CN=1)C.[C:58](=[O:61])([O-])O.[Na+].CN(C)[CH:65]=[O:66]>>[CH3:65][O:66][C:44]1[CH:45]=[C:34]([CH:33]=[CH:48][C:43]=1[O:61][CH3:58])[CH2:35][NH:36][C:18](=[O:20])[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][CH:11]([NH:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:12]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
7
Procedure
Veratolylamine (257 mg) and the compound prepared in Example 222 (350 mg) were dissolved in dimethylformamide (2 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydro-chloride (256 mg), 1-hydroxybenzotriazole (227 mg), and dimethylaminopyridine (10 mg) were added to the solution. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol]t to give the title compound (310 mg).
Workup
- extractionthe mixture was extracted with chloroform-propanol (3/1)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was removed by distillation under the reduced pressure
- customThe residue was purified by HPLC [chloroform/methanol]t
Sources & evidence
- ORD record
- ord-cad1e9738e0f4120ab0354abbfc46cbb
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217722B2
Reaction notes
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