Hydrochloric Acid → HCID 178436864, compound

HRID 1198651Notes

Reaction equation

HRID 1198651 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][O:12][C:13]3[C:22]4[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=4[N:16]=[C:15]([CH2:23][CH3:24])[CH:14]=3)[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[C:3]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[NH:42][N:41]=[N:40][N:39]=1.Cl>C(O)C.[OH-].[Na+]>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][O:12][C:13]3[C:22]4[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=4[N:16]=[C:15]([CH2:23][CH3:24])[CH:14]=3)[CH:9]=2)[NH:4][C:3]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[NH:42][N:41]=[N:40][N:39]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178436863HCID 178436863, compound

Product 1

HCID 178436864HCID 178436864, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

1,1-Dimethylethyl 3-bromo-5-[[2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy]methyl]-2-[2-(1H-tetrazol-5-yl)phenyl]-1H-indole-1-carboxylate (A) (100 mg) in a mixture of ethanol (15 ml) and 2M aqueous sodium hydroxide solution (5 ml) is heated at 60° C. for 3 hours. The mixture is cooled and acidified with 2M hydrochloric acid to pH 5 to 6. The mixture is then extracted with dichloromethane and the combined extracts are dried (MgSO4) and evaporated to give 3-bromo-5-[[2-ethyl-5,6,7,8-tetrahydroquinolin-4-yloxy]methyl]-2-[2-(1H-tetrazol-5-yl)phenyl]-1H-indole.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe mixture is then extracted with dichloromethane
  3. dry with materialthe combined extracts are dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-758bbbec1af8447b95897df27f4df8d7
Source dataset
uspto-grants-1994_01
Patent number
US05281613

Reaction notes

Loading…