Hydrochloric Acid → 3-(6,7-Dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-2-oxoindoline-5-carbonitrile hydrochloride

HRID 1777198Notes

Reaction equation

HRID 1777198 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]2[C:13]1[N:18]=[C:17]2[CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][C:16]2=[CH:15][CH:14]=1)#[N:2].[ClH:29]>O1CCOCC1>[ClH:29].[N:18]1[C:13]([CH:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:8][C:7]2=[O:12])=[CH:14][CH:15]=[C:16]2[CH2:21][NH:20][CH2:19][C:17]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66823532HCID 66823532, compound

Product 1

HCID 668234033-(6,7-Dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-2-oxoindoline-5-carbonitrile hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of tert-butyl 2-(5-cyano-2-oxoindolin-3-yl)-5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate (70 mg, 0.186 mmol) in dioxane (2 mL) was added dropwise 4N HCl in dioxane (2.5 mL). After stirring the resulting mixture at RT for 3 d all volatiles were removed under reduced pressure. The residue was suspended in diethylether and stirred at RT for 2 h. The suspension was filtered, the remaining solid was washed with diethylether and dried under reduced pressure. Amount 55 mg. Yield 95%.

Workup

  1. customwere removed under reduced pressure
  2. stirringstirred at RT for 2 h
  3. filtrationThe suspension was filtered
  4. washthe remaining solid was washed with diethylether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9fb9db44acd3412f859c911e5398f84f
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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