Sodium Iodide → HCID 71533204, compound

HRID 1774789Notes

Reaction equation

HRID 1774789 reaction equation
Cl[CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[C:19](=[O:25])[CH2:18][CH2:17]3)[CH:11]=[N:12][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].Cl.[CH2:35]([NH2:37])[CH3:36].C([O-])(O)=O.[Na+]>CC#N.CCOC(C)=O>[CH2:35]([NH:37][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[C:19](=[O:25])[CH2:18][CH2:17]3)[CH:11]=[N:12][CH:13]=1)[CH3:36]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 11198Ethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86679152HCID 86679152, compound

Product 1

HCID 71533204HCID 71533204, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed tube, a solution of 6-[5-((S)-2-chloromethyl-pyrrolidin-1-yl)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one (0.066 g, 0.185 mmol) in CH3CN (2.5 mL) was mixed with K2CO3 (0.064 g, 0.464 mmol), TEA (0.188 g, 1.85 mmol), sodium iodide (0.028 g, 0.185 mmol) and ethanamine hydrochloride (0.151 g, 1.85 mmol). The reaction mixture was then heated to 80° C. over night. The mixture was diluted with EtOAc, poured into aq. NaHCO3 (10 mL) and the aqueous layer was extracted with EtOAc (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography, eluting with a 0 to 15% MeOH(1% NH4OH)-DCM gradient to give the title compound (0.02 g, 30%) as an orange gum. MS: 365.2 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  2. washCombined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a 0 to 15% MeOH(1% NH4OH)-DCM gradient

Sources & evidence

ORD record
ord-0248b9458b2548498a86446c1f390eae
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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