Ammonium Carbonate → 2-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carboxylic acid [2-(4-amino-butylcarbamoyl)-ethyl]phenyl-amide

HRID 68190Notes

Reaction equation

HRID 68190 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:45])[CH2:14][CH2:15][N:16]([C:23]([C:25]1[CH:44]=[CH:43][C:28]2[N:29]([CH3:42])[C:30]([CH2:32][NH:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)=[N:31][C:27]=2[CH:26]=1)=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C)(C)C.C(=O)([O-])[O-].[NH4+:51].[NH4+]>Cl.C(O)C>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH2:14][CH2:15][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]([C:25]1[CH:44]=[CH:43][C:28]2[N:29]([CH3:42])[C:30]([CH2:32][NH:33][C:34]3[CH:39]=[CH:38][C:37]([C:40](=[NH:41])[NH2:51])=[CH:36][CH:35]=3)=[N:31][C:27]=2[CH:26]=1)=[O:24])=[O:45]

Participants

5

Reactant 2

HCID 517111Ammonium CarbonateHCID 66706504{4-[3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionylamino]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 533274672-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carboxylic acid [2-(4-amino-butylcarbamoyl)-ethyl]phenyl-amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The product of 1f (4.81 mmol) was dissolved in a saturated solution of HCl in ethanol (250 mL), the mixture stirred at room temperature over night and then evaporated to dryness at 30° C. The remaining raw material was dissolved in 200 mL dry ethanol, then ammonium carbonate (48.1 mmol) was added and the mixture stirred at room temperature over night. After evaporation of the solvent the remaining raw material was triturated with ca. 5 mL ethanol, the undissolved material separated by filtration and the solvent evaporated at 30° C. The product was then dissolved in 30 mL water, the solution stirred with ca. 2 g charcoal, filtered and evaporated to dryness.

Workup

  1. customevaporated to dryness at 30° C
  2. dissolutionThe remaining raw material was dissolved in 200 mL dry ethanol
  3. stirringthe mixture stirred at room temperature over night
  4. customAfter evaporation of the solvent the remaining raw material
  5. customwas triturated with ca. 5 mL ethanol
  6. customthe undissolved material separated by filtration
  7. customthe solvent evaporated at 30° C
  8. dissolutionThe product was then dissolved in 30 mL water
  9. stirringthe solution stirred with ca. 2 g charcoal
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-8f6931dbce994389892705f0d0639f67
Source dataset
uspto-grants-2014_09
Patent number
US08821871B2

Reaction notes

Loading…