Benzonitrile, 2-amino-4-chloro- → HCID 86707775, compound

HRID 2410127Notes

Reaction equation

HRID 2410127 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)O)=[O:5])[CH3:2].[NH2:24][C:25]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1[CH:11]([NH:24][C:25]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 170059Benzonitrile, 2-amino-4-chloro-HCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate

Product 1

HCID 86707775HCID 86707775, compound

Procedure

The title compound was prepared in analogy to the procedure described for step E2 but using intermediate B and 2-amino-4-chlorobenzonitrile. The reaction mixture was stirred at rt for 20 h. The mixture was extracted with HCl 1M and with a saturated aqueous NaHCO3 solution. The organic layers were dried (Na2SO4), filtered and concentrated. The product was triturated in Et2O, the suspension was filtered and the solid was dried in HV. tR: 1.36 min (LC-MS 2); ESI-MS: 535.2/537.2/539.1 [M+H]+ (LC-MS 2).

Workup

  1. extractionThe mixture was extracted with HCl 1M and with a saturated aqueous NaHCO3 solution
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was triturated in Et2O
  6. filtrationthe suspension was filtered
  7. customthe solid was dried in HV

Sources & evidence

ORD record
ord-e5fbed8ad3d04e2d816cb872defeb7c5
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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