Ammonia → HCID 59587465, compound

HRID 1410426Notes

Reaction equation

HRID 1410426 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[NH:12][C:13]=2[C:14](O)=[O:15])=[CH:5][CH:4]=1.O.OC1C2N=N[NH:30]C=2C=CC=1.N.O1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[NH:12][C:13]=2[C:14]([NH2:30])=[O:15])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 59587421HCID 59587421, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59587465HCID 59587465, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxyphenyl)-2-(pyridin-4-yl)-1H-imidazole-5-carboxylic acid (0.090 g, 0.3 mmol) and hydroxybenzotriazole monohydrate (0.047 g, 0.3 mmol) in DMF (2.5 ml) was added 0.5M ammonia in dioxane (2 m, 1.0 mmol) and the resulting solution stirred at room temperature for 10 minutes. 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide (0.064 g, 0.33 mmol) was added and the reaction mixture stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford 4-(4-methoxyphenyl)-2-(pyridin-4-yl)-1H-imidazole-5-carboxamide (0.025 g, 0.08 mmol, 67%). 1H NMR (DMSO) 3.83 (3H, s), 7.03 (2H, d), 7.20 (1H, br. s), 7.50 (1H, br. s), 7.84 (2H, d), 8.03 (2H, dd), 8.68 (2H, dd), 13.12 (1H, br. s). LCMS (2) Rt 1.68 min; m/z (ES+) 295.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-96ade6794dc84578a3280bb379383a6a
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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