1,2-Dichloroethane → HCID 178432874, compound

HRID 1875180Notes

Reaction equation

HRID 1875180 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[C:12]([Cl:20])=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:22][C:23]1[N:24]=[C:25]([CH3:31])[NH:26][C:27]=1[C:28](O)=[O:29].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(O)(C(F)(F)F)=O>CCOC(C)=O>[Cl:22][C:23]1[N:24]=[C:25]([CH3:31])[NH:26][C:27]=1[C:28]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:13]([C:14]#[N:15])[C:12]=2[Cl:20])[C:4]=1[F:21])=[O:29]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 684876593-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrileHCID 178432882HCID 178432882, compound

Product 1

HCID 178432874HCID 178432874, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile (60 mg, 0.174 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (27.9 mg, 0.174 mmol) and HOBT (26.6 mg, 0.174 mmol) was added EDC (33.3 mg, 0.174 mmol) and the reaction mixture was stirred at rt for 2 hours. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-({4-chloro-3-[(2,5-dichloro-3-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (28 mg, 0.046 mmol, 27% yield) as the TFA salt. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.66 (d, 1H), 7.29-7.49 (m, 2H), 6.97 (s, 1H), 4.64 (s, 2H), 2.34 (s, 3H). LC-MS (ES+) m/z 486.93, [M+H].

Workup

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-6e57f6a6414948619fea63a0c7791942
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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