1,2-Dichloroethane → HCID 178432869, compound

HRID 1875172Notes

Reaction equation

HRID 1875172 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Br:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:21][C:22]1[N:23]=[C:24]([CH3:30])[NH:25][C:26]=1[C:27](O)=[O:28].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:19][C:17]1[CH:18]=[C:11]([O:10][C:5]2[C:4]([F:20])=[C:3]([CH2:2][NH:1][C:27]([C:26]3[NH:25][C:24]([CH3:30])=[N:23][C:22]=3[Cl:21])=[O:28])[CH:8]=[CH:7][C:6]=2[Cl:9])[CH:12]=[C:13]([C:14]#[N:15])[CH:16]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 68485937HCID 68485937, compoundHCID 178432882HCID 178432882, compound

Product 1

HCID 178432869HCID 178432869, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (900 mg, 2.53 mmol) and 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (813 mg, 2.53 mmol) in DMF (10 ml) was added HOBT (388 mg, 2.53 mmol) and EDC (485 mg, 2.53 mmol) and the reaction mixture was stirred for 6 hours at rt. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give N-({3-[(3-bromo-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-2-methyl-1H-imidazole-5-carboxamide (0.560 g, 1.124 mmol, 44% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.68 (s, 1H), 7.29-7.45 (m, 3H), 7.25 (s, 1H), 4.63 (s, 2H), 2.34 (s, 3H). LC-MS (ES+) m/z 496.87, [M+H].

Workup

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-d94992ce5deb455c8a1507463462c190
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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