Hydrochloric Acid → HCID 24800587, compound

HRID 1991482Notes

Reaction equation

HRID 1991482 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([CH:21]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:22]([NH:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[C:19]3[CH:37]=[CH:38][CH:39]=[CH:40][C:18]=3[N:17]=2)=[CH:12][CH:11]=1.N1C=CC=CC=1.Cl>ClCCl>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([CH:21]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[C:22]([NH:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:23])[C:19]3[CH:37]=[CH:38][CH:39]=[CH:40][C:18]=3[N:17]=2)=[CH:12][CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 7918Acetic Anhydride2×HCID 68694033HCID 68694033, compound

Product 1

HCID 24800587HCID 24800587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (175 mg, 1.71 mmol, 1.0 equiv.) was added to a solution of 2-[2-(4-amino-phenyl)-benzoimidazol-1-yl]-2,N-dicyclohexyl-acetamide hydrogen chloride (example 34) (74 mg, 1.71 mmol, 1.0 equiv.) and pyridine (13 mg, 1.71 mmol, 1.0 equiv.) in dichloromethane (2 mL). The reaction was stirred at room temperature for 16 hours then retreated with pyridine (13 mg, 1.71 mmol, 1.0 equiv.) and acetic anhydride (17 mg, 0.17 mmol, 0.1 equiv.) and stirred at room temperature for a further 24 hours. The reaction mixture was added to 1 N HCl (2 mL) and the resultant precipitate was filtered and washed with dichloromethane. The solid was dissolved in hot ethyl acetate (3 mL) and filtered, the filtrate was concentrated in vacuo to afford 2-[2-(4-acetylamino-phenyl)-benzoimidazol-1-yl]-2,N-dicyclohexyl-acetamide as a cream solid, 26 mg (32%), MS (ES+): 473 (M+H).

Workup

  1. stirringstirred at room temperature for a further 24 hours
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with dichloromethane
  4. dissolutionThe solid was dissolved in hot ethyl acetate (3 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f4516c28bb2d4c66bfe18420047a3eb9
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

Loading…