Sodium Bicarbonate → HCID 66818134, compound

HRID 1754911Notes

Reaction equation

HRID 1754911 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]([NH2:27])([C:25]#[N:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])(O)=O.[Na+]>CCO>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][C:22]([C:25]#[N:26])([NH:27][C:6]([C:5]2[CH:9]=[CH:10][N:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:8])[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 8199422-Methoxyisonicotinic AcidHCID 22091429tert-Butyl 4-amino-4-cyanopiperidine-1-carboxylate

Product 1

HCID 66818134HCID 66818134, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride 2,7-hydrate (1.06 g, 3.26 mmol) was added to a solution of 2-methoxy-isonicotinic acid (500 mg, 3.26 mmol) and 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (669 mg, 2.97 mmol) in EtOH (8.0 ml) at room temperature, and the mixture was stirred for 46.5 hours. An aqueous NaHCO3 solution was added to the reaction mixture, followed by extraction with AcOEt three times. The organic layers were washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (CH2Cl2/MeOH=99:1 to 95:5) to give 4-cyano-4-[(2-methoxy-pyridine-4-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless form (901 mg, 84%).

Workup

  1. extractionfollowed by extraction with AcOEt three times
  2. washThe organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (CH2Cl2/MeOH=99:1 to 95:5)

Sources & evidence

ORD record
ord-f3123588ecfb40d1b36e625842acfeb9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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