Dimethylformamide → HCID 69148452, compound
Reaction equation
ON1C2C=C[CH:9]=[CH:10][C:5]=2N=N1.Cl.[CH3:12]N(C)CCCN=C=NCC.[OH:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]3[S:33][C:34]([C:36]([OH:38])=O)=[CH:35][N:30]3[C:29]=2[CH:39]=1.[OH-].[Na+].[CH3:42][N:43]([CH:45]=O)C>>[OH:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]3[S:33][C:34]([C:36]([N:43]([CH3:42])[CH2:45][C:10]([CH3:9])([CH3:5])[CH3:12])=[O:38])=[CH:35][N:30]3[C:29]=2[CH:39]=1Participants
Procedure
In an ice bath, 1-hydroxybenzotriazole (2.03 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.75 g) were added to a DMF (25 ml) suspension of 6-hydroxymethylthiazolo[3,2-a]benzimidazole-2-carboxylic acid (2.48 g), and the reaction mixture was stirred for 30 minutes in the ice bath and then for 2 hours by removing the ice bath. Methylneopentylamine hydrochloride (2.75 g) and triethylamine (2.8 ml) were added to the reaction mixture, and the resulting reaction mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into 1 M sodium hydroxide aqueous solution (50 ml). The insoluble matter was collected by filtration, washed with water (150 ml) and then dried by heating under a reduced pressure to obtain the pale yellow title compound (1.98 g).
Workup
- customfor 2 hours by removing the ice bath
- additionMethylneopentylamine hydrochloride (2.75 g) and triethylamine (2.8 ml) were added to the reaction mixture
- customthe resulting reaction mixture
- customAfter completion of the reaction
- filtrationThe insoluble matter was collected by filtration
- washwashed with water (150 ml)
- customdried
- temperatureby heating under a reduced pressure
Sources & evidence
- ORD record
- ord-0336d28b27c0458186284d7902e2ab43
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250429B2
Reaction notes
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