Sodium Methoxide → N-(4-{(E)-2-[3-tert-Butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-3-methoxymethyl-phenyl)-methanesulfonamide

HRID 2390858Notes

Reaction equation

HRID 2390858 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:6]=[CH:7][C:8]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[C:15]([C:17]2[C:18](=[O:25])[NH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:14]=[C:13]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:12]=1[O:30][CH3:31].[CH3:37][O-:38].[Na+]>CO>[C:26]([C:13]1[C:12]([O:30][CH3:31])=[C:11](/[CH:10]=[CH:9]/[C:8]2[CH:7]=[CH:6][C:5]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])=[CH:4][C:3]=2[CH2:2][O:38][CH3:37])[CH:16]=[C:15]([C:17]2[C:18](=[O:25])[NH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:14]=1)([CH3:28])([CH3:29])[CH3:27]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68540957N-(3-bromomethyl-4-{(E)-2-[3-tert-butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-phenyl)-methanesulfonamide

Product 1

HCID 67070255N-(4-{(E)-2-[3-tert-Butyl-2-methoxy-5-(6-methoxy-2-oxo-1,2-dihydro-pyridin-3-yl)-phenyl]-vinyl}-3-methoxymethyl-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

step 3—A solution of 324 (93 mg, 0.162 mmol) in MeOH (10 mL) and sodium methoxide (10 mL, 5 mmol, 0.5 M methanol solution) was stirred at RT overnight. The reaction mixture was concentrated, diluted with EtOAc and acidified with 6N HCl (1 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The crude product was purified on a preparative TLC plate developed with 2:1 EtOAc/hexane to afford 26 mg (31%) of I-209 as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on a preparative TLC plate
  8. customto afford 26 mg (31%) of I-209 as an off-white solid

Sources & evidence

ORD record
ord-4a339d8984fd40bdb99933a83cd87412
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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