Hydrochloric Acid → (E)-1-(2,6-dichloro-3-fluorophenyl)-N-[6-(1-piperidin-4-ylpyrazol-4-yl)pyrrolo[3,2-b]pyridin-1-yl]methanimine

HRID 1404616Notes

Reaction equation

HRID 1404616 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1/[CH:10]=[N:11]/[N:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[CH:25]=3)[CH:19]=2)[CH:14]=[CH:13]1.Cl>CO>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1/[CH:10]=[N:11]/[N:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]4)[CH:25]=3)[CH:19]=2)[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 87408523tert-butyl 4-[4-[1-[(E)-(2,6-dichloro-3-fluorophenyl)methylideneamino]pyrrolo[3,2-b]pyridin-6-yl]pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 87408679(E)-1-(2,6-dichloro-3-fluorophenyl)-N-[6-(1-piperidin-4-ylpyrazol-4-yl)pyrrolo[3,2-b]pyridin-1-yl]methanimineYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-[4-(1-{[(E)-(2,6-dichloro-3-fluorophenyl)methylidene]amino}-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (15 mg, 0.027 mmol) in MeOH (0.5 mL) was treated with HCl (4.0M solution in dioxane, 2.0 mL) at room temperature for 2 h. Solvents were removed and the residue was treated with aqueous NaHCO3, and extracted with ethyl acetate. The organic layer was dried, evaporated to afford the desired intermediate as a yellowish solid (6.5 mg, yield 53%).

Workup

  1. customSolvents were removed
  2. additionthe residue was treated with aqueous NaHCO3
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-a659ca1196664dbbb474f7c73f542675
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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