Sodium Methoxide → HCID 178451954, compound

HRID 931191Notes

Reaction equation

HRID 931191 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)=O)=[CH:6][CH:5]=[C:4]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([C:30]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[CH2:25]2)[N:3]=1.C[O-].[Na+]>CO.C(O)(CC)C.CO>[N:32]1([C:30]([CH:26]2[CH2:27][CH2:28][CH2:29][N:24]([C:4]3[N:3]=[C:2]4[NH:1][C:9]([C@@H:11]5[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]5)=[N:8][C:7]4=[CH:6][CH:5]=3)[CH2:25]2)=[O:31])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 117966487tert-butyl 3-((2-amino-6-((R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)carbamoyl)piperidine-1-carboxylate

Product 1

HCID 178451954HCID 178451954, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 19940262Methanol sec-butanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 3-((2-amino-6-((R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)carbamoyl)piperidine-1-carboxylate in methanol/sec-butanol (1:2, 15 mL) was added a solution of 25% sodium methoxide in methanol (9.0 mL). The reaction mixture was stirred at 90° C. for 16 h. The solvent was removed under reduced pressure and a solution of methanol/dichloromethane (1:9, 50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) were added to the residue, and the layers were separated. The aqueous layer was extracted again with methanol/dichloromethane (1:9, 25 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via column chromatography to afford (R)-tert-butyl 3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-yl)piperidine-1-carboxylate.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiona solution of methanol/dichloromethane (1:9, 50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) were added to the residue
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted again with methanol/dichloromethane (1:9, 25 mL)
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via column chromatography

Sources & evidence

ORD record
ord-429ac089a0674a629dad7d735ffe6c61
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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