2-Methyl-2-butene → HCID 69558982, compound

HRID 1833197Notes

Reaction equation

HRID 1833197 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[O:20][CH3:21])[C:16]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH3:31])[CH:24]=2)=[N:15][CH:14]=[C:13]3[CH:33]=[O:34])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.P([O-])(O)(O)=[O:37].[Na+].CC(=CC)C.[Cl:47]([O-])=O.[Na+]>C(O)(C)(C)C.O>[ClH:47].[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][C:19]=2[O:20][CH3:21])[C:16]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH3:31])[CH:24]=2)=[N:15][CH:14]=[C:13]3[C:33]([OH:37])=[O:34])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 22048412HCID 22048412, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 69558982HCID 69558982, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of 6-(3-pyrrolidin-1-yl-propoxy)-7-methoxy-1-(3-ethoxy-benzoyl)-isoquinoline-4-carbaldehyde (63 mg, 0.13 mmol) in t-butanol (0.5 mL) and water (0.5 mL) solution was added sodium dihydrogenphosphate monohydrate (73 mg, 0.53 mmol), 2-methyl-2-butene (0.089 mL, 0.80 mmol) and sodium chlorite (71.2 mg, 0.80 mmol) at room temperature. The reaction suspension was then stirred at room temperature for 14 hrs. The resulting two-phase mixture was partitioned between dichloromethane and water and acidified to pH=3 by addition of 1N hydrochloric acid. The aqueous phase was then extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated sodium chloride solution (30 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a brown semi-solid oil. The crude product was recrystallized in ethyl acetate to afford 6-(3-pyrrolidin-1-yl-propoxy)-1-(3-ethoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid hydrochloride (20 mg, 32% yield) as a light brown solid. HR-MS m/e calcd for C27H30N2O6 (M−H+) 479.2177, found 479.2182; 1H NMR (300 MHz) compatible.

Workup

  1. customThe resulting two-phase mixture was partitioned between dichloromethane and water
  2. additionacidified to pH=3 by addition of 1N hydrochloric acid
  3. extractionThe aqueous phase was then extracted with dichloromethane (3×20 mL)
  4. washThe combined extracts were washed with saturated sodium chloride solution (30 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a brown semi-solid oil
  9. customThe crude product was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-cbcc1a8e9eec461a9d14d9f3e0e2d424
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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