Hydrochloric Acid → HCID 67059656, compound

HRID 220406Notes

Reaction equation

HRID 220406 reaction equation
[CH:1]1([N:4]([CH:31]2[CH2:33][CH2:32]2)[C:5]([C:7]2[N:28]([CH2:29][CH3:30])[C:10]3=[N:11][C:12]([NH:19][C:20]4[CH:24]=[C:23]([CH:25]=O)[N:22]([CH3:27])[N:21]=4)=[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.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[CH:1]1([N:4]([CH:31]2[CH2:33][CH2:32]2)[C:5]([C:7]2[N:28]([CH2:29][CH3:30])[C:10]3=[N:11][C:12]([NH:19][C:20]4[CH:24]=[C:23]([CH2:25][N:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)[N:22]([CH3:27])[N:21]=4)=[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

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86651856HCID 86651856, compound

Product 1

HCID 67059656HCID 67059656, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N,N-dicyclopropyl-6-ethyl-4-(5-formyl-1-methyl-1H-pyrazol-3-ylamino)-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 112B, 22 mg, 0.049 mmol) and molecular seives 4 Å (30 mg) in MeOH (2 mL) was added morpholine (0.017 mL, 0.197 mmol). After the solution was stirred at room temperature for 12 hrs, sodium borohydride (7.46 mg, 0.197 mmol) was then added and stirred for 3 hrs. The solution was brought to pH=4 with 1N HCl, neutralized with saturated aqueous sodium bicarbonate, and then extracted with CH2Cl2. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica-gel flash chromatography using an Isco 40 g column eluting from 0-10% MeOH/CH2Cl2 to yield N,N-dicyclopropyl-6-ethyl-1-methyl-4-(1-methyl-5-(morpholinomethyl)-1H-pyrazol-3-ylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (14.3 mg, 0.027 mmol, 54.9% yield) as a white solid.

Workup

  1. stirringstirred for 3 hrs
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica-gel flash chromatography
  6. washeluting from 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-3df7ec06d966440ea6655a1ae8faa144
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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