Water → HCID 14994963, compound
Reaction equation
[NH2:1][C:2]1[S:17][C:5]2[CH2:6][N:7]([C:10]([O:12][CH2:13][CH2:14][C:15]#[CH:16])=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25].N1C=CC=CC=1.[Br:33][CH:34]([CH3:38])[C:35](Br)=[O:36].O>O1CCOCC1>[Br:33][CH:34]([CH3:38])[C:35]([NH:1][C:2]1[S:17][C:5]2[CH2:6][N:7]([C:10]([O:12][CH2:13][CH2:14][C:15]#[CH:16])=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])=[O:36]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1.35 g of 2-amino-3-(2-chlorobenzoyl)-6-(3-butynyloxycarbonyl)-4,5,6,7-tetrahydro-thieno[2,3-C]pyridine was dissolved in 20 ml of dioxane, to which 0.33 g of pyridine was added, followed by dropping at 0° C. 0.90 g of 2-bromopropionyl bromide. After completion of the reaction, the reaction mixture was charged into water, extracted with dichloromethane and dried with anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography (elution solvent: dichloromethane:hexane=1:1-1.0), thereby obtaining 1.19 g of the intended compound.
Workup
- additionwas added
- customby dropping at 0° C
- customAfter completion of the reaction
- extractionextracted with dichloromethane
- dry with materialdried with anhydrous magnesium sulfate
- distillationafter which the solvent was distilled off under reduced pressure
- customThe resultant residue was purified by silica gel column chromatography (elution solvent: dichloromethane:hexane=1:1-1.0)
Sources & evidence
- ORD record
- ord-993522a9cb0f44ae8b4111fb858ab2e6
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05482937
Reaction notes
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