Hydrochloric Acid → HCID 86710371, compound

HRID 1398378Notes

Reaction equation

HRID 1398378 reaction equation
C([O:3][C:4]([C:6]1[C:22]([O:23][CH2:24][C@@H:25]([NH:30]C(=O)OC(C)(C)C)[CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:21][C:9]2[N:10]([CH3:20])[C:11](=[O:19])[C:12]3[C:17]([C:8]=2[CH:7]=1)=[CH:16][CH:15]=[N:14][C:13]=3[CH3:18])=[CH2:5])C.Cl.O1CCOCC1>>[C:4]([C:6]1[C:22]([O:23][CH2:24][C@@H:25]([NH2:30])[CH2:26][CH:27]([CH3:28])[CH3:29])=[CH:21][C:9]2[N:10]([CH3:20])[C:11](=[O:19])[C:12]3[C:17]([C:8]=2[CH:7]=1)=[CH:16][CH:15]=[N:14][C:13]=3[CH3:18])(=[O:3])[CH3:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86710369HCID 86710369, compound

Product 1

HCID 86710371HCID 86710371, compoundYield 42%

Procedure

(S)-tert-Butyl (1-((9-(1-ethoxyvinyl)-4,6-dimethyl-5-oxo-5,6 dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (200 mg, 0.392 mmol) was treated with hydrochloric acid in 1,4-dioxane (981 μL, 3.92 mmol) at 0° C. The reaction mixture was allowed to stir at RT for 2 h and then evaporated to dryness. The crude material was neutralized with aqueous 10% NaHCO3 and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated which afforded (S)-9-acetyl-8-((2-amino-4-methylpentyl)oxy)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.11 g, 0.164 mmol, 42% yield) as brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 382.2 [(M+H)+, calcd for C22H28N3O3, 382.2]; LC/MS retention time (method E): tR=0.78 min.

Workup

  1. customevaporated to dryness
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated which

Sources & evidence

ORD record
ord-9c2ea29713e3429d92bbe9a691afcf0f
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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