4-Aminobenzonitrile → HCID 18412521, compound

HRID 50383Notes

Reaction equation

HRID 50383 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-methoxymethylthieno[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 sulfate and filtered. The filtrate was mixed with 14 mL of N-ethyldiisopropylamine 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 50° 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. washthe mixture was washed with 20 mL of saturated sodium hydrogen carbonate solution
  2. customthe organic phase was separated off
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. distillationThen the methylene chloride was distilled off in vacuo
  6. customthe residue obtained
  7. temperaturewas heated to 50° 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-aba60fc238f94c399c5fd84700ef9659
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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