Hydrochloric Acid → HCID 90408074, compound

HRID 2277551Notes

Reaction equation

HRID 2277551 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][N:18]=2)[N:14]=[CH:13]1)[CH3:2].[NH4+].[Cl-].[N-:27]=[N+:28]=[N-:29].[Na+].Cl.[OH-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[C:21]([C:23]3[N:27]=[N:28][NH:29][N:24]=3)[CH:20]=[CH:19][N:18]=2)[N:14]=[CH:13]1)[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 90407760HCID 90407760, compound

Product 1

HCID 90408074HCID 90408074, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 2-[1-[2-(2-ethoxyphenyl)ethyl]imidazol-4-yl]pyridine-4-carbonitrile (1 eq) and NH4Cl (10 eq) in DMF was added NaN3 at rt, then stirred for 2 hr at 110° C. in a microwave oven, LC/MS showed the reaction was completed, acidified to PH=3-4 by conc. HCl, stirred for 1 hr, then adjusted to PH=7-8 by NaOH, concentrated and purified by HPLC to give the title compound (56%). 1H NMR (400 MHz, DMSO): δ 1.36 (3H, t, J=6.4 Hz), 3.06-3.09 (2H, m), 4.02-4.03 (2H, m), 4.25-4.29 (2H, m), 6.82-7.19 (4H, m), 7.69 (1H, s), 7.76-7.81 (2H, m), 8.47 (1H, s), 8.61 (1H, d, J=6.0 Hz). [M+H] Calc'd for C19H19N7O, 362. Found, 362.

Workup

  1. stirringstirred for 1 hr
  2. concentrationconcentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-9afd03e18746456fa9f0d63cb31bbb22
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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