Hydrochloric Acid → 2-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carboxylic acid [2-(2-amino-ethylcarbamoyl)-ethyl]pyridin-2-yl-amide

HRID 449747Notes

Reaction equation

HRID 449747 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][C:11](=[O:43])[CH2:12][CH2:13][N:14]([C:21]([C:23]1[CH:42]=[CH:41][C:26]2[N:27]([CH3:40])[C:28]([CH2:30][NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(C)(C)C.Cl.C(=O)([O-])[O-].[NH4+:50].[NH4+]>C(O)C>[NH2:7][CH2:8][CH2:9][NH:10][C:11]([CH2:12][CH2:13][N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:21]([C:23]1[CH:42]=[CH:41][C:26]2[N:27]([CH3:40])[C:28]([CH2:30][NH:31][C:32]3[CH:33]=[CH:34][C:35]([C:38](=[NH:39])[NH2:50])=[CH:36][CH:37]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])=[O:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 66706334{2-[3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionylamino]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 667065732-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carboxylic acid [2-(2-amino-ethylcarbamoyl)-ethyl]pyridin-2-yl-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product of 2b (1.34 mmol) was added to a saturated HCl solution in dry ethanol (30 mL). The solution was stirred at room temperature for 5 hours, then evaporated to dryness at 30° C. Ethanol (30 mL) and ammonium carbonate (13.0 mmol) were added and the mixture stirred at room temperature over night. The solvent was then evaporated, the residual material was triturated 5 times with ca. 4 mL of a mixture of dichloromethane/methanol (30:1), filtered and evaporated in order to separate the product from inorganic salts.

Workup

  1. customevaporated to dryness at 30° C
  2. stirringthe mixture stirred at room temperature over night
  3. customThe solvent was then evaporated
  4. customthe residual material was triturated 5 times with ca. 4 mL of a mixture of dichloromethane/methanol (30:1)
  5. filtrationfiltered
  6. customevaporated in order
  7. customto separate the product from inorganic salts

Sources & evidence

ORD record
ord-38869121d3de4222933255d2184000bc
Source dataset
uspto-grants-2013_07
Patent number
US08486398B2

Reaction notes

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