Hydrochloric Acid → HCID 178523893, compound

HRID 895383Notes

Reaction equation

HRID 895383 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[NH:18])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[C:27]([N:34]1[CH:38]=[CH:37]N=C1)(N1C=CN=C1)=[O:28].[Cl:39][C:40]1[CH:45]=[CH:44]C(CN)=[CH:42][CH:41]=1.Cl>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:16][C:17]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)=[N:18][C:27]([NH:34][CH2:38][C:37]1[CH:44]=[CH:45][C:40]([Cl:39])=[CH:41][CH:42]=1)=[O:28])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178512031HCID 178512031, compound

Product 1

HCID 178523893HCID 178523893, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-[1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)-ethyl]-N′-(4-chlorophenyl)guanidine of Example 231 (step B) in THF was added carbonyldimidazole. The reaction mixture was allowed to stir at rt for 2 h, then 4-chlorophenylmethylamine was added. This was allowed to stir at rt for 18 h. The solvent was removed and the residue partitioned between EtOAc and ammonium chloride solution. The organic layer was separated, dried, concentrated, and purified by silica gel column chromatography (EtOAc, MeOH, NH4OH; 90:10:0.1) to give an oil. The oil was dissolved in MEOH, and to this was added HCl solution in ether. The solvent was removed to give the title compound as a solid. MS (ES): r/z 576 [M+H]+.

Workup

  1. stirringto stir at rt for 18 h
  2. customThe solvent was removed
  3. customthe residue partitioned between EtOAc and ammonium chloride solution
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (EtOAc, MeOH, NH4OH; 90:10:0.1)
  8. customto give an oil
  9. dissolutionThe oil was dissolved in MEOH
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-49462e7e1f1d4fa4acbed03a9d538801
Source dataset
uspto-grants-2005_07
Patent number
US06916813B2

Reaction notes

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