1,2-Dichloroethane → HCID 178510236, compound

HRID 1875249Notes

Reaction equation

HRID 1875249 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[C:11]([F:29])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[C:24]([CH:26]([F:28])[F:27])[CH:25]=2)[C:21]#[N:22])[C:13]([Cl:16])=[CH:14][CH:15]=1.[Br:30][C:31]1[N:32]=[CH:33][NH:34][C:35]=1[C:36](O)=[O:37].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:30][C:31]1[N:32]=[CH:33][NH:34][C:35]=1[C:36]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][C:18]2[CH:25]=[C:24]([CH:26]([F:28])[F:27])[CH:23]=[C:20]([C:21]#[N:22])[CH:19]=2)[C:11]=1[F:29])=[O:37]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 867616563-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetateHCID 1785249144-bromo-1H-imidazole-5-carboxylic acid

Product 1

HCID 178510236HCID 178510236, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetate (90 mg, 0.204 mmol), 4-bromo-1H-imidazole-5-carboxylic acid (39.0 mg, 0.204 mmol) and HOBT (31.3 mg, 0.204 mmol) in DMF (3 ml) was added EDC (39.1 mg, 0.204 mmol) and the reaction mixture was stirred at RT for 30 minutes. The crude material was purified via reverse phase HPLC to give the title compound (56 mg, 55% yield). 1H NMR (DMSO-d6) δ ppm 8.42 (br. s., 1H) 7.85 (s, 1H) 7.79 (s, 1H) 7.72 (s, 1H) 7.47-7.58 (m, 2H) 7.38 (t, 1H) 7.07 (t, 1H) 4.51 (d, 2H). LC-MS (ES+) m/z 499.00 [M+H].

Workup

  1. customThe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-27b5b7f9584f4ee19ccffc858fd880b0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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