Dichloromethane → HCID 71117035, compound

HRID 629891Notes

Reaction equation

HRID 629891 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH:13]3[CH:18]([OH:19])[CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14]3)=[CH:10][CH:11]=2)[N:6]([CH3:27])[C:5]1=[O:28].C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>CCOC(C)=O>[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([CH:13]3[C:18](=[O:19])[CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:14]3)=[CH:10][CH:11]=2)[N:6]([CH3:27])[C:5]1=[O:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 71136214HCID 71136214, compound

Product 1

HCID 71117035HCID 71117035, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added tert-butyl 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-hydroxypiperidine-1-carboxylate (20-5) (25 mg, 0.060 mmol), DCM (1 mL), and Dess-MartinPeriodinane (27.9 mg, 0.066 mmol), and the resulting mixture was then stirred under an atmosphere of nitrogen at room temperature for 15 hours. The reaction mixture was then suspended in EtOAc, and washed with a saturated solution of Na2S2O3, followed by a saturated solution of sodium bicarbonate, then water, and finally brine. Organics dried over sodium sulfate, filtered & concentrated to give crude tert-butyl 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-oxopiperidine-1-carboxylate (22-1). LRMS (M+H)+: observed=417.4, calculated=417.5.

Workup

  1. washwashed with a saturated solution of Na2S2O3
  2. dry with materialOrganics dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04e84011ae274779803a4593ac947e36
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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