Sodium Bicarbonate → HCID 66670255, compound

HRID 1514656Notes

Reaction equation

HRID 1514656 reaction equation
[NH2:1][C:2]([NH2:29])=[N:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]C)[N:8]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:7]=1[CH3:28])=[O:5].[Cl:30]CCl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[ClH:30].[NH2:29][C:2]([NH2:1])=[N:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[N:8]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[C:7]=1[CH3:28])=[O:5]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 66670261HCID 66670261, compound

Product 1

HCID 66670255HCID 66670255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 400 mg portion of N-(diaminomethylene)-1-[2-(4-fluorophenyl)ethyl]-5-(2-methoxyphenyl)-2-methyl-1H-pyrrole-3-carboxamide was dissolved in 10 ml of dichloromethane, and 3.04 ml of a 1 M boron tribromide dichloromethane solution was added dropwise thereto at −70° C. under an atmosphere of argon, followed by stirring at room temperature for 15 hours. Then, 100 ml of a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by three times extractions with 20% methanol/chloroform. After drying the organic layer with anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (Chromatorex (registered trademark), methanol:chloroform=10:90-20:80). Then, the resulting product was dissolved in 3 ml of ethyl acetate and, under ice-cooling, 0.132 ml of 4 M hydrogen chloride/ethyl acetate was added, followed by stirring overnight at room temperature. The resulting solid was collected by filtration to obtain 90 mg of N-(diaminomethylene)-1-[2-(4-fluorophenyl)ethyl]-5-(2-hydroxyphenyl)-2-methyl-1H-pyrrole-3-carboxamide hydrochloride as a white solid.

Workup

  1. customat −70° C.
  2. extractionfollowed by three times extractions with 20% methanol/chloroform
  3. dry with materialAfter drying the organic layer with anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Chromatorex (registered trademark), methanol:chloroform=10:90-20:80)
  6. dissolutionThen, the resulting product was dissolved in 3 ml of ethyl acetate and, under ice-
  7. temperaturecooling
  8. addition0.132 ml of 4 M hydrogen chloride/ethyl acetate was added
  9. stirringby stirring overnight at room temperature
  10. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-971edf9a0a4e485ab31e277bc7c6c208
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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