Water → HCID 14994963, compound

HRID 1588344Notes

Reaction equation

HRID 1588344 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

HCID 962WaterHCID 1049PyridineHCID 79047Propanoyl bromide, 2-bromo-HCID 14994962HCID 14994962, compound

Product 1

HCID 14994963HCID 14994963, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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

  1. additionwas added
  2. customby dropping at 0° C
  3. customAfter completion of the reaction
  4. extractionextracted with dichloromethane
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationafter which the solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography (elution solvent: dichloromethane:hexane=1:1-1:0)

Sources & evidence

ORD record
ord-992172d35b08457daf95f622e478422a
Source dataset
uspto-grants-1993_06
Patent number
US05221671

Reaction notes

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