5-((Diphenylmethylene)amino)-N-methoxy-N-methylnicotinamide → HCID 90094063, compound

HRID 1753047Notes

Reaction equation

HRID 1753047 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][C:8]([N:11]1[C:19]2[C:18]([F:20])=[CH:17][N:16]=[CH:15][C:14]=2[C:13](I)=[CH:12]1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[C:29](=[N:42][C:43]1[CH:44]=[N:45][CH:46]=[C:47]([CH:54]=1)[C:48](N(OC)C)=[O:49])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[C:29](=[N:42][C:43]1[CH:54]=[C:47]([C:48]([C:13]2[C:14]3[CH:15]=[N:16][CH:17]=[C:18]([F:20])[C:19]=3[N:11]([C:8]([CH3:10])([CH3:9])[CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:23])[CH3:22])[CH:12]=2)=[O:49])[CH:46]=[N:45][CH:44]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 866720805-((Diphenylmethylene)amino)-N-methoxy-N-methylnicotinamideHCID 90093713HCID 90093713, compoundHCID 178418339Butyllithium

Product 1

HCID 90094063HCID 90094063, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring solution of 1-[2-(tert-Butyl-dimethyl-silyloxy)-1,1-dimethyl-ethyl]-7-fluoro-3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 73, 3 g, 6.69 mmol) in dry ether (100 mL) at −78° C., n-BuLi (3.9 mL, 1.84M, 7.17 mmol) was added and stirred for 30 minutes. Then 5-(benzhydrylidene-amino)-N-methoxy-N-methyl-nicotinamide (Preparation 52, 2.31 g, 6.69 mmol) in dry ether (10 mL) was added drop wise for 5 min. After 1 hr reaction mixture was quenched with saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and evaporated in vacuo to afford the crude compound, purified by silica gel column chromatography eluting with Ethyl acetate: Hexane 30:70 to 35:65 to afford the title compound as a light red solid (25%, 1 g).

Workup

  1. customAfter 1 hr reaction mixture
  2. customwas quenched with saturated aqueous solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated in vacuo
  6. customto afford the crude compound
  7. custompurified by silica gel column chromatography
  8. washeluting with Ethyl acetate: Hexane 30:70 to 35:65

Sources & evidence

ORD record
ord-4682f40e251943408f5c9d320166e467
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

Loading…