1,1'-Carbonyldiimidazole → HCID 136050684, compound

HRID 1767382Notes

Reaction equation

HRID 1767382 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH2:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[N:3]=1.[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31]>C1COCC1>[OH:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[C:7]2[CH2:8][NH:9][C:30](=[O:31])[NH:1][C:2]=2[N:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 135550591HCID 135550591, compound

Product 1

HCID 136050684HCID 136050684, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a cold (0° C.) solution of tert-butyl 3-[2-amino-3-(aminomethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]-1-piperidinecarboxylate (0.020 g, 0.050 mmol) in THF (2.0 mL) under an argon atmosphere was added 1,1′-carbonyldiimidazole (0.009 g, 0.055 mmol). After stirred for 15 min, the mixture was quenched with saturated sodium bicarbonate solution. The resulting mixture was partitioned between ethyl acetate and saturated ammonium chloride solution. The separated organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (2.0 mL). The mixture was heated at 60° C. for 1 hr and allowed to cool to room temperature. The resulting precipitates were collected by filtration, washed with ethyl acetate and dried under reduced pressure to give tert-Butyl 3-[7-(2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-5-yl]-1-piperidinecarboxylate. (0.007 g, yield; 33%)

Workup

  1. customthe mixture was quenched with saturated sodium bicarbonate solution
  2. customThe resulting mixture was partitioned between ethyl acetate and saturated ammonium chloride solution
  3. washThe separated organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (2.0 mL)
  8. temperatureto cool to room temperature
  9. customThe resulting precipitates
  10. filtrationwere collected by filtration
  11. washwashed with ethyl acetate
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-849c87704a854c3aa4a43e5a4da632cc
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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