Hydrochloric Acid → N-benzyl-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

HRID 1404612Notes

Reaction equation

HRID 1404612 reaction equation
[CH2:1]([NH:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[CH:22]=3)[CH:16]=2)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([NH:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH:22]=3)[CH:16]=2)[CH:11]=[CH:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67458095tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

Product 1

HCID 58532480N-benzyl-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amineYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate (25 mg, 0.053 mmol) in MeOH (0.3 mL) was treated with HCl (4.0M solution in dioxane, 1.5 mL) at room temperature for 30 min. Solvents were evaporated and the residue was diluted with aq. NaHCO3, extracted with ethyl acetate. The organic layer was dried, filtered and evaporated to give a white solid (10 mg, yield 51%).

Workup

  1. customSolvents were evaporated
  2. additionthe residue was diluted with aq. NaHCO3
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3791328c92394789b4478d2ac7a26b14
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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