Sodium Bicarbonate → HCID 58636802, compound

HRID 1158973Notes

Reaction equation

HRID 1158973 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH3:36])=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=2)[C:22]=1[CH:23](O)[CH3:24])[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:48])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH3:36])=[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=2)[C:22]=1[CH:23]([F:48])[CH3:24])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][C:20]1[N:19]=[CH:18][C:17]2[CH2:16][N:7]([C:8]3[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=3)[C:6](=[O:37])[O:5][CH:23]([CH3:24])[C:22]=2[C:21]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 58636730HCID 58636730, compound

Product 2

HCID 58636802HCID 58636802, compoundYield 43%HCID 58636809HCID 58636809, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(3-cyano-benzyloxy)-4-(1-hydroxy-ethyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (112) (245 mg, 0.10 mol) in dry dichloromethane (7 mL) was slowly added bis(2-methoxyethyl)aminosulfur trifluoride (350 mg, 1.6 mol) at 0° C. under nitrogen atmosphere. The reaction was slowly warmed to room temperature and stirred for 30 minutes. 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 ethyl acetate:hexane (0:1 to 1:1) as an eluant to give [5-(3-cyano-benzyloxy)-4-(1-fluoro-ethyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (113) (54 mg, 22% yield) and 4-[3,5-dimethyl-4-(3-cyano-benzyloxy)-7-oxo-5,9-dihydro-6-oxa-2,8-diaza-benzocyclohepten-8-yl]-benzonitrile (114) (90 mg, 43% yield).

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 ethyl acetate:hexane (0:1 to 1:1) as an eluant

Sources & evidence

ORD record
ord-3b1eca1ad7b240359e909c1cd1dbe40a
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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