Triethylamine → 4-fluoro-benzenesulfonic acid 2-amino-3-cyclopropanecarbonyl-3H-benzoimidazol-5-yl ester

HRID 1823772Notes

Reaction equation

HRID 1823772 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:17][C:11]=2[N:10]=1.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1.C(N(CC)CC)C>ClCCl>[NH2:8][C:9]1[N:10]([C:32]([CH:29]2[CH2:31][CH2:30]2)=[O:33])[C:11]2[CH:17]=[C:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)(=[O:20])=[O:21])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 178508205HCID 178508205, compound

Product 1

HCID 865960754-fluoro-benzenesulfonic acid 2-amino-3-cyclopropanecarbonyl-3H-benzoimidazol-5-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.53 g of 4-fluoro-benzenesulfonic acid 2-amino-1H-benzoimidazol-5-yl ester trifluoroacetic acid salt were combinated with 1.8 ml of cyclopropanecarbonylchloride and 5 ml triethylamine in 75 ml dichloromethane. Reaction mixture was stirred at room temperature for 1 hour. Solvents were evaporated under reduced pressure. The residue was then taken up in dichloromethane, washed with water and dried with magnesium sulfate. Dichloromethane was evaporated under reduced pressure and precipitate obtained was dried on glass frit yielding 4.88 g of 4-fluoro-benzenesulfonic acid 2-amino-3-cyclopropanecarbonyl-3H-benzoimidazol-5-yl ester.

Workup

  1. customReaction mixture
  2. customSolvents were evaporated under reduced pressure
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. customDichloromethane was evaporated under reduced pressure and precipitate
  6. customobtained
  7. customwas dried on glass frit

Sources & evidence

ORD record
ord-f850c72495774ee9b2ebd6576ec661d3
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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