Potassium Carbonate → HCID 71280887, compound

HRID 2401139Notes

Reaction equation

HRID 2401139 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.Cl[C:13]1[N:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][C:21]3([CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:20]2=[O:29])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][N:9]([C:13]2[N:14]=[CH:15][C:16]([N:19]3[CH2:23][CH2:22][C:21]4([CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:20]3=[O:29])=[CH:17][N:18]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59401808(2S,3'S)-2-Methyl-[1,3]bipyrrolidinyl2×HCID 86677571HCID 86677571, compound

Product 1

HCID 71280887HCID 71280887, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl (0.072 g, 0.315 mmol) in acetonitrile (25 mL) was added 2-(2-chloro-pyrimidin-5-yl)-8-oxa-2-aza-spiro[4.5]decan-1-one (0.07 g, 0.262 mmol), and powdered potassium carbonate (0.145 g, 1.05 mmol) and stirred at 70° C. for 16.0 hours. Additional (2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl (0.1 g) was added and reaction mixture stirred for 4 hours at 70° C. The reaction mixture was then allowed to cool to room temperature, quenched with water (2 mL) diluted with ethyl acetate (10 mL). The aqueous phase was extracted with 10% methanol in dichloromethane (10 ml, 3×), combined organics washed with brine, dried over Na2SO4, concentrated under vacuum. Purification by column chromatography on silica gel (0-100%) eluting with methanol in dichloromethane (0-10%) afforded 0.0732 g (72%) of the title compound.

Workup

  1. customreaction mixture
  2. stirringstirred for 4 hours at 70° C
  3. temperatureto cool to room temperature
  4. customquenched with water (2 mL)
  5. additiondiluted with ethyl acetate (10 mL)
  6. extractionThe aqueous phase was extracted with 10% methanol in dichloromethane (10 ml, 3×)
  7. washcombined organics washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under vacuum
  10. customPurification by column chromatography on silica gel (0-100%)
  11. washeluting with methanol in dichloromethane (0-10%)

Sources & evidence

ORD record
ord-f032573031b349449a518e13357e5ca9
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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