Hydrochloric Acid → HCID 135887182, compound

HRID 1627234Notes

Reaction equation

HRID 1627234 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9]([C:11]2[N:12](COCC[Si](C)(C)C)[C:13]([CH3:31])=[C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)=[CH:19]4)[N:15]=2)=[O:10])=[CH:3][CH:2]=1.Cl.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(O)C.C(OCC)C.O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][NH:8][C:9]([C:11]2[NH:12][C:13]([CH3:31])=[C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20]([C:25]3[O:29][N:28]=[C:27]([CH3:30])[N:26]=3)=[CH:19]4)[N:15]=2)=[O:10])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 136341015HCID 136341015, compound

Product 1

HCID 135887182HCID 135887182, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-Methyl-4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indol-5-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid 4-pyridylmethyl amide (12.6 g, 19 6 mmoL) in ethanol (70 ml) is added aqueous HCl (6N 50 ml, 300 mmol). The mixture is heated at 100° C. for 7 hours. After cooling to room temperature, the resulting suspension is diluted with ice-cooled water (500 ml), basified with saturated aqueous NaHCO3 (50 ml) and aqueous sodium hydroxide (5N, 46.5 ml) to pH 7-8. Diethylether is added, (50 ml) and suspension stirred for 30 minutes. The resulting suspension is filtered and the solids are washed with water (2×50 ml), ether (2×25 ml), dried at 60° C. in vacuo for 14 hours to give a solid that is triturated with 1:1 acetonitrile-ethanol (40 ml) to give the product 5.75 g, 80%, LC/MS ESI m/z (M+H)+=414.5.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe resulting suspension is diluted with ice-
  3. filtrationThe resulting suspension is filtered
  4. washthe solids are washed with water (2×50 ml), ether (2×25 ml)
  5. customdried at 60° C. in vacuo for 14 hours
  6. customto give a solid
  7. customthat is triturated with 1:1 acetonitrile-ethanol (40 ml)

Sources & evidence

ORD record
ord-76c7a595e8a34afca799f1cb298672c4
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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