Ethanolamine → 4-[(4-{3-[2-Cyano-3-(2-hydroxyethyl)guanidino]propoxy}phenyl)methyl]-3-(beta-d-glucopyranosyloxy)-5-isopropyl-1h-pyrazole
Reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[N:45][C:46]#[N:47])SC)=[CH:33][CH:32]=2)=[C:28]([CH:48]([CH3:50])[CH3:49])[NH:27][N:26]=1)(=O)C.[NH2:51][CH2:52][CH2:53][OH:54].C[O-].[Na+]>CO>[C:46]([N:45]=[C:42]([NH:51][CH2:52][CH2:53][OH:54])[NH:41][CH2:40][CH2:39][CH2:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:48]([CH3:50])[CH3:49])=[CH:36][CH:35]=1)#[N:47]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-[(4-{3-[N′-(cyano)-S-(methyl)isothioureido]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole (30 mg) in methanol (1 mL) was added 2-aminoethanol (0.5 mL), and the mixture was stirred at 50° C. overnight. After cooling to room temperature, to the reaction mixture was added sodium methoxide (28% methanol solution, 0.02 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (15 mg).
Workup
- temperatureAfter cooling to room temperature, to the reaction mixture
- stirringthe mixture was stirred at room temperature for 1 hour
- concentrationThe reaction mixture was concentrated under reduced pressure
- distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
Sources & evidence
- ORD record
- ord-593bd8e6845d4dedbe4ad096150df733
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324176B2
Reaction notes
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