Hydrochloric Acid → HCID 86685960, compound

HRID 2277670Notes

Reaction equation

HRID 2277670 reaction equation
C([SiH2][O:6][C:7](C)(C)[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]1[CH:14]=[C:15]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([Cl:29])[CH:25]=3)[C:20]2=[O:30])[CH:16]=[N:17][CH:18]=1)(C)(C)C.Cl.O1CCOCC1>CO>[Cl:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:30])[N:19]([C:15]1[CH:16]=[N:17][CH:18]=[C:13]([N:9]3[CH2:10][CH2:11][CH2:12][C@H:8]3[CH2:7][OH:6])[CH:14]=1)[CH2:28][CH2:27]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178455461HCID 178455461, compound

Product 1

HCID 86685960HCID 86685960, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-{5-[(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-pyridin-3-yl}-6-chloro-3,4-dihydro-2H-isoquinolin-1-one (0.110 g, 0.233 mmol) in MeOH (2 mL) was added 4M HCl in dioxane (0.233 ml, 0.932 mmol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was evaporated to dryness, the residue was diluted with DCM (20 mL) and washed with NaHCO3 (10 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH (1% NH4OH)-DCM gradient to give the title compound (0.06 g, 72%) as a light yellow solid. MS: 358.0 (M+H+).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthe residue was diluted with DCM (20 mL)
  3. washwashed with NaHCO3 (10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with a 0 to 5% MeOH (1% NH4OH)-DCM gradient

Sources & evidence

ORD record
ord-d406a3a0f55044d08617ddf5ecc5be89
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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