4-Aminobenzonitrile → HCID 18412521, compound

HRID 2288518Notes

Reaction equation

HRID 2288518 reaction equation
[C:1]1([N:7]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:8]([C:10]2[S:21][C:13]3[N:14]=[C:15]([CH2:18]OC)[N:16]([CH3:17])[C:12]=3[CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(N(C(C)C)C(C)C)C.[NH2:41][C:42]1[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=1>C(Cl)Cl.N.C(Cl)Cl.C(O)C>[C:1]1([N:7]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:8]([C:10]2[S:21][C:13]3[N:14]=[C:15]([CH2:18][NH:41][C:42]4[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=4)[N:16]([CH3:17])[C:12]=3[CH:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 133964-AminobenzonitrileHCID 25134Boron tribromideHCID 81531DiisopropylethylamineHCID 184125131-Methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

Product 1

HCID 18412521HCID 18412521, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 6344DichloromethaneSolvent2×HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of 0.73 g (1.88 mmol) of 1-methyl-2-methoxymethyl-thieno[2.3-d]imidazol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)-amide in 30 ml of methylene chloride were added dropwise at 5° C. 2.9 ml (2.9 mmol) of a 1-molar solution of boron tribromide in methylene chloride. After 16 hours' stirring at ambient temperature the mixture was washed with 20 ml of saturated sodium hydrogen carbonate solution, the organic phase was separated off, dried with sodium sulphate and filtered. The filtrate was mixed with 14 ml of N-ethyl-diisopropylamine and 0.43 g (3.64 mmol) of 4-aminobenzonitrile. Then the methylene chloride was distilled off in vacuo, the residue obtained was heated to 5° C. for 1 hour and then the residual solvent was distilled off in vacuo. After chromatography (silica gel; methylene chloride/ethanol=99:1 to 97:3) a yellow oil was obtained which slowly solidified. Yield: 0.37 g (42% of theory), Rf value: 0.29 (silica gel; methylene chloride/ethanol=50:1+a few drops of ammonia)

Workup

  1. washwas washed with 20 ml of saturated sodium hydrogen carbonate solution
  2. customthe organic phase was separated off
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. distillationThen the methylene chloride was distilled off in vacuo
  6. customthe residue obtained
  7. temperaturewas heated to 5° C. for 1 hour
  8. distillationthe residual solvent was distilled off in vacuo
  9. customAfter chromatography (silica gel; methylene chloride/ethanol=99:1 to 97:3) a yellow oil was obtained which

Sources & evidence

ORD record
ord-1a55095d660d43ab8cc453b644690386
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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