Acetic Anhydride → HCID 178432465, compound

HRID 536688Notes

Reaction equation

HRID 536688 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([N:19]3[CH2:26][CH2:25][C:24]4([CH3:30])[C:27]([CH3:29])([CH3:28])[CH:20]3[CH2:21][C:22]3[CH:34]=[C:33]([C:35]([NH:37]O)=[NH:36])[CH:32]=[CH:31][C:23]=34)=[O:18])=[CH:16][C:11]=2[N:10]=[CH:9]1>CC1C=C(C)C=C(C)N=1>[NH:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([N:19]3[CH2:26][CH2:25][C:24]4([CH3:30])[C:27]([CH3:28])([CH3:29])[CH:20]3[CH2:21][C:22]3[CH:34]=[C:33]([C:35]5[N:36]=[C:5]([CH3:6])[O:7][N:37]=5)[CH:32]=[CH:31][C:23]=34)=[O:18])=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178421475HCID 178421475, compound

Product 1

HCID 178432465HCID 178432465, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

Acetic anhydride (0.1 mL) is added to a solution of 3-(1H-benzoimidazole-5-carbonyl)-N-hydroxy-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-9-carboxamidine (0.15 g) in 2,4,6-trimethylpyridine (2 mL). The resulting solution is stirred at ambient temperature for 1 h and then at 120° C. for 3 h. After cooling to room temperature, the mixture is concentrated under reduced pressure and the residue is taken up in methanol (10 mL). Concentrated aqueous ammonia solution (1 mL) is added and the solution is stirred at ambient temperature for 1 h. The solution is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (water/MeCN) to give the title compound as a white foam-like solid.

Workup

  1. waitat 120° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additionConcentrated aqueous ammonia solution (1 mL) is added
  5. stirringthe solution is stirred at ambient temperature for 1 h
  6. concentrationThe solution is concentrated under reduced pressure
  7. customthe residue is purified by HPLC on reversed phase (water/MeCN)

Sources & evidence

ORD record
ord-f501eb8ce0c34c2b971484e97e7e2c44
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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