Sodium Bicarbonate → HCID 58636750, compound

HRID 1158970Notes

Reaction equation

HRID 1158970 reaction equation
[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH3:35])=[C:21]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[CH:28]=2)[C:22]=1[CH2:23]O)[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:47])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH3:35])=[C:21]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[CH:28]=2)[C:22]=1[CH2:23][F:47])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58636738HCID 58636738, compound

Product 1

HCID 58636750HCID 58636750, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (106) (51.1 g, 0.10 mol) in dry dichloromethane (700 mL) was slowly added bis(2-methoxyethyl)aminosulfur trifluoride (39.7 g, 0.18 mol) at 0° C. under nitrogen atmosphere. The reaction was slowly warmed to room temperature and stirred for 2 hours. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of dichloromethane:acetone (1:0 to 18:1) as an eluant to give [5-(3-cyano-benzyloxy)-4-fluoromethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (107) (41.3 g, 80% yield) as a colorless solid.

Workup

  1. customat 0° C.
  2. extractionthe crude product extracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a crude residue, which
  6. customwas purified by column chromatography on silica gel using
  7. additiona gradient mixture of dichloromethane:acetone (1:0 to 18:1) as an eluant

Sources & evidence

ORD record
ord-4be63150c9d14af7b3a1a3b6b2f19d63
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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