Hydrochloric Acid → HCID 178479661, compound

HRID 521420Notes

Reaction equation

HRID 521420 reaction equation
[O:1]=[C:2]1[C:25]2[C:6]3=[C:7]([CH:22]=[CH:23][CH:24]=2)[NH:8][C:9]2[CH2:10][N:11](C(OC(C)(C)C)=O)[CH2:12][CH2:13][C:14]=2[C:5]3=[N:4][NH:3]1.[ClH:26]>O1CCOCC1>[ClH:26].[N:4]1[NH:3][C:2](=[O:1])[C:25]2[C:6]3[C:5]=1[C:14]1[CH2:13][CH2:12][NH:11][CH2:10][C:9]=1[NH:8][C:7]=3[CH:22]=[CH:23][CH:24]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451560HCID 178451560, compound

Product 1

HCID 178479661HCID 178479661, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 3-oxo-7,8,10,11-tetrahydro-2H-phthalazino[8,1-bc][1,7]naphthyridine-9(3H)-carboxylate (100 mg) in dioxane (6 mL) was added con.HCl (2.0 mL) dropwise, the mixture was then stirred at room temperature for 0.5 h. The solvent was evaporated in vacuo and water (10 mL) was added. The mixture was washed with methylene dichloride (20 mL), and the aqueous phase was evaporated to afford 8,9,10,11-tetrahydro-2H-phthalazino[8,1-bc][1,7]naphthyridin-3(7H)-one hydrochloride (46 mg, 57%). 1H NMR (DMSO-d6) δ 11.9 (s, 1H), 10.95 (s, 1H), 9.59 (s, 1H), 7.34-7.69 (m, 3H), 3.33-3.51 (m, 4H), 2.55-2.56 (m, 2H). MS (ESI) m/e [M+1]+241.0.

Workup

  1. customThe solvent was evaporated in vacuo and water (10 mL)
  2. additionwas added
  3. washThe mixture was washed with methylene dichloride (20 mL)
  4. customthe aqueous phase was evaporated

Sources & evidence

ORD record
ord-b0f4d5ff2d47451b8e5b96b024b2fe45
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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