Chloroacetone → N,N-dicyclopropyl-6-ethyl-1-methyl-4-(4-methylthiazol-2-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

HRID 220351Notes

Reaction equation

HRID 220351 reaction equation
[CH:1]1([N:4]([CH:26]2[CH2:28][CH2:27]2)[C:5]([C:7]2[N:23]([CH2:24][CH3:25])[C:10]3=[N:11][C:12]([NH:19][C:20]([NH2:22])=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.Cl[CH2:30][C:31](=O)[CH3:32]>CCO>[CH:26]1([N:4]([CH:1]2[CH2:2][CH2:3]2)[C:5]([C:7]2[N:23]([CH2:24][CH3:25])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][CH:30]=[C:31]([CH3:32])[N:22]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 58180527N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Product 1

HCID 58180630N,N-dicyclopropyl-6-ethyl-1-methyl-4-(4-methylthiazol-2-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamideYield 20.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-dicyclopropyl-6-ethyl-1-methyl-4-thioureido-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 2B, 40 mg, 0.10 mmol) and chloroacetone (62.4 mg, 0.40 mmol) in EtOH (2 ml) were heated at 80° C. for 20 min. The reaction was cooled to room temperature and the solvent removed in vacuo. Saturated NaHCO3 solution was added and the aqueous layer extracted (3×) with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (dichloromethane/methanol 0-7%) to provide N,N-dicyclopropyl-6-ethyl-1-methyl-4-(4-methylthiazol-2-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (9 mg, 12% yield) as a white solid.

Workup

  1. customthe solvent removed in vacuo
  2. additionSaturated NaHCO3 solution was added
  3. extractionthe aqueous layer extracted (3×) with dichloromethane
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography (dichloromethane/methanol 0-7%)

Sources & evidence

ORD record
ord-222ff99b1ba24b8eae13454fe6aa4a6e
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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