Hydrochloric Acid → HCID 178468697, compound

HRID 1096974Notes

Reaction equation

HRID 1096974 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:7]1[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[CH:21]1[CH2:23][CH2:22]1)#[N:6].Cl.C(N(CC)CC)C.Cl>C(OCC)(=O)C.CN(C=O)C>[CH:21]1([N:11]2[C:12]3[C:8](=[C:7]([C:5]4[NH:6][N:3]=[N:2][N:1]=4)[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=3)[CH:9]=[CH:10]2)[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 57930989Ethyl 4-cyano-1-cyclopropyl-1H-indole-6-carboxylate

Product 1

HCID 178468697HCID 178468697, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In a 100-mL egg plant-type flask, sodium azide (486 mg, 7.48 mmol) was added to a DMF (10 mL) solution of ethyl 4-cyano-1-cyclopropyl-1H-indole-6-carboxylate (475 mg, 1.87 mmol) and triethylamine hydrochloride (1.03 g, 7.48 mmol), and stirred overnight at 110° C. The reaction solution was diluted with ethyl acetate, made acidic with aqueous hydrochloric acid solution added thereto, and the separated organic layer was washed with water and saturated saline water in that order, dried with sodium sulfate, filtered and concentrated. The crude product was washed with hexane to obtain the title compound as a colorless solid.

Workup

  1. additionadded
  2. washthe separated organic layer was washed with water and saturated saline water in that order
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-bb9209bd04bd438682f5c7ebe878ded3
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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