tert-Butyl 2-(5-cyano-2-oxoindolin-3-yl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate → 2-Oxo-3-(5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)indoline-5-carbonitrile

HRID 1777190Notes

Reaction equation

HRID 1777190 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[CH:22]=[CH:21][C:20]2[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][C:15]=2[N:14]=1)#[N:2]>Cl.O1CCOCC1>[O:12]=[C:7]1[CH:6]([C:13]2[CH:22]=[CH:21][C:20]3[CH2:19][NH:18][CH2:17][CH2:16][C:15]=3[N:14]=2)[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8]1

Participants

4

Reactant 1

HCID 66823325tert-Butyl 2-(5-cyano-2-oxoindolin-3-yl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 569483732-Oxo-3-(5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)indoline-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(5-cyano-2-oxoindolin-3-yl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (73 mg, 0.187 mmol) in 4N HCl in dioxane (5 mL) was stirred at RT for 3 h. After this period all volatiles were removed in vacuo. The residue was dissolved in water and washed with ethyl acetate. The aqueous layer was neutralized with saturated solution of sodium bicarbonate and extracted with ethyl acetate. The latter extracts were dried over sodium sulfate, filtered, and evaporated to dryness. Quant. yield.

Workup

  1. customAfter this period all volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe latter extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-1630322b14c340128619326cb20eba86
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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