1,2-Dichloroethane → 2-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide

HRID 1875084Notes

Reaction equation

HRID 1875084 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Br:23])=[CH:21][CH:22]=1.[N:35]([C:38]1[NH:39][C:40]([C:44](O)=[O:45])=[C:41]([Cl:43])[N:42]=1)=[N+:36]=[N-:37]>CN(C=O)C.CCOC(C)=O>[N:35]([C:38]1[NH:39][C:40]([C:44]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[C:19]([O:24][C:25]3[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=3)[C:18]=2[F:34])=[O:45])=[C:41]([Cl:43])[N:42]=1)=[N+:36]=[N-:37]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 1785145302-azido-4-chloro-1H-imidazole-5-carboxylic acid

Product 1

HCID 1785099102-azido-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamideYield 103.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (0.331 g, 1.726 mmol) and HOBT (0.233 g, 1.726 mmol) were added to a solution of 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.558 g, 1.569 mmol) and 2-azido-4-chloro-1H-imidazole-5-carboxylic acid (0.294 g, 1.569 mmol) in DMF (7 mL). The mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with water and brine and the organic layer was dried over sodium sulfate and concentrated to give the crude title compound (0.850 g) as a light yellow solid. This crude product was taken on to the next step without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5f10dc3a15984854be9b11d4dca82415
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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