Sodium Hydroxide → N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

HRID 220350Notes

Reaction equation

HRID 220350 reaction equation
C([NH:9][C:10](=[S:36])[NH:11][C:12]1[N:17]=[C:16]2[N:18]([CH2:30][CH3:31])[C:19]([C:21]([N:23]([CH:27]3[CH2:29][CH2:28]3)[CH:24]3[CH2:26][CH2:25]3)=[O:22])=[CH:20][C:15]2=[C:14]2[N:32]([CH3:35])[CH:33]=[N:34][C:13]=12)(=O)C1C=CC=CC=1.[OH-].[Na+]>CCO>[CH:27]1([N:23]([CH:24]2[CH2:25][CH2:26]2)[C:21]([C:19]2[N:18]([CH2:30][CH3:31])[C:16]3=[N:17][C:12]([NH:11][C:10]([NH2:9])=[S:36])=[C:13]4[N:34]=[CH:33][N:32]([CH3:35])[C:14]4=[C:15]3[CH:20]=2)=[O:22])[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 581806324-(3-benzoylthioureido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Product 1

HCID 58180527N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3-Benzoylthioureido)-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 2A, 306 mg, 0.61 mmol) and 1N NaOH (10 ml, 10.00 mmol) in 10 ml EtOH were heated at 60° C. for 1 h. The reaction was cooled to room temperature and concentrated. The remaining aqueous solution was extracted (3×) with ethyl acetate. The organic phase was dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography (dichloromethane/methanol 0-4%) gave N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide as a yellow solid (199 mg, 82% yield).

Workup

  1. concentrationconcentrated
  2. extractionThe remaining aqueous solution was extracted (3×) with ethyl acetate
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (dichloromethane/methanol 0-4%)

Sources & evidence

ORD record
ord-6397cb373cc149308b941f845c91c2be
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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