Hydrochloric Acid → HCID 118037102, compound

HRID 1778118Notes

Reaction equation

HRID 1778118 reaction equation
[C:1]([C:3]1[C:4]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[N:20]=[C:19]([CH:22](OC)[O:23]C)[C:18]([CH:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[CH:17][C:16]=3[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].Cl>O1CCOCC1.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[C:4]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[C:19]([CH:22]=[O:23])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 118036967HCID 118036967, compound2×

Product 1

HCID 118037102HCID 118037102, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of tert-butyl 4-(8-((5-cyano-4-isopropoxypyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)piperidine-1-carboxylate (intermediate 338, 55 mg) and 4N HCl in dioxane (0.35 ml) was stirred at room temperature. After 3 h, additional 4N HCl in dioxane (0.15 ml) was added. After 5 h, the reaction mixture was diluted with sat. aq. NaHCO3 and extracted with DCM (3×). The combined organic phases were dried over Na2SO4 and evaporated. The residue was triturated with Et2O to give the title compound as a white solid.

Workup

  1. waitAfter 5 h
  2. extractionextracted with DCM (3×)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-5cf3e6986f954db88e7ea4f3e5129c0c
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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