Ammonium Chloride → HCID 15949743, compound

HRID 646272Notes

Reaction equation

HRID 646272 reaction equation
[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=[O:28])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.[CH3:31][CH2:32][Mg+].[Br-].[Cl-].[NH4+]>C1COCC1.ClCCl>[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH:27]([OH:28])[CH2:31][CH3:32])[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15949563HCID 15949563, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 15949743HCID 15949743, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

A mixture of 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-ethyl-1H-pyrrole-2-carbaldehyde (0.10 g; 0.25 mmol) in THF (5 mL; anhydrous) was stirred and cooled to −15° C. To this was added an excess of EtMgBr (3.1 eq; 0.25 mL of 3.0 M solution in hexane), dropwise. The mixture was stirred at −15° C. for one hour. The reaction was worked up by carefully adding 1.0 mL of saturated aqueous ammonium chloride solution, diluting with dichloromethane (30 mL) and washing with water. The organic phase was dried over MgSO4, filtered and evaporated. Two products were separated from the crude mixture by chromatography on silica gel. The column was eluted with a chloroform/methanol mixture on a gradient (9:1 through 7:3). The more polar product was isolated and crystallized from ethyl acetate/hexane to give the title product as white crystals, 0.05 g (46% yield), mp 115-121° C.; MS (ES) m/z 434.2; [M−H]−

Workup

  1. stirringThe mixture was stirred at −15° C. for one hour
  2. washwashing with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customTwo products were separated from the crude mixture by chromatography on silica gel
  7. washThe column was eluted with a chloroform/methanol mixture on a gradient (9:1 through 7:3)
  8. customThe more polar product was isolated
  9. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-39eefce149b0493c9a364425af3eed46
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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