Pyridine → HCID 66740717, compound

HRID 1627328Notes

Reaction equation

HRID 1627328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([NH2:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].N1C=CC=CC=1.[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:34]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:34]=1[C:35]([NH:23][C:14]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:11]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:24][CH3:25])[CH:4]=2)([CH3:10])[CH3:9])=[CH:12][N:13]=1)=[O:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27365472-Chloro-6-fluorobenzoyl chlorideHCID 66740747HCID 66740747, compound

Product 1

HCID 66740717HCID 66740717, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-amine (93 mg, 0.26 mmol) and pyridine (0.05 mL, 0.52 mmol) in DCM (1.5 mL) was added 2-chloro-6-fluorobenzoyl chloride (0.050 g, 0.26 mmol) in DCM (0.5 mL). After stirring 2 h at ambient temperature, the reaction was quenched with water. The mixture was extracted with DCM (3×5 mL) and dried with MgSO4. The residue was purified by HPLC (10-99%, MeCN/H2O with 0.05% TFA) to afford the title compound (9 mg) as a white solid. MS (EI) m/z 516 [M+H]+.

Workup

  1. customthe reaction was quenched with water
  2. extractionThe mixture was extracted with DCM (3×5 mL)
  3. dry with materialdried with MgSO4
  4. customThe residue was purified by HPLC (10-99%, MeCN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-d181f3fc541c4a84adec5c4063905b73
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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