Hydrochloric Acid → 7-Bromo-2-(2-(tert-butyl(5-(thiophen-2-yl)pent-4-ynyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

HRID 1971648Notes

Reaction equation

HRID 1971648 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:35])[C:18]([N:20]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:21][CH2:22][CH2:23][C:24]#[C:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:36][CH3:37].[OH-].[K+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:35])[C:18]([N:20]([C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:21][CH2:22][CH2:23][C:24]#[C:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:36][CH3:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124904Ethyl 7-bromo-2-(2-(tert-butyl(5-(thiophen-2-yl)pent-4-ynyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Product 1

HCID 581249487-Bromo-2-(2-(tert-butyl(5-(thiophen-2-yl)pent-4-ynyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3.1 g of 3b in 30 ml of dioxane and a solution of 1.5 g of KOH in 10 ml of water were mixed and stirred for 3 hr at RT. 75 ml of water was added and the mixture was acidified with 0.5N HCl to pH3. The product was extracted with ethyl acetate. The material 3c which remained after washing, drying and concentration was used, as such, in the cyclization step.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washafter washing
  3. customdrying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-00ed955bdb9f42f89045938f5a5ea0c4
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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