Chloride → HCID 59327163, compound

HRID 410326Notes

Reaction equation

HRID 410326 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=3)=[CH:23][N:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[C:31](Cl)(=[O:33])[CH3:32].[Cl-].C(N(CC)CC)C>O.C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][N:28]([C:31](=[O:33])[CH3:32])[CH2:29][CH:30]=3)=[CH:23][N:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

7

Reactant 4

HCID 312ChlorideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59326831HCID 59326831, compound

Product 1

HCID 59327163HCID 59327163, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added (1H-benzo[d]imidazol-2-yl)(4-(5-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidin-4-yloxy)phenyl)methanone (60.8 mg, 0.153 mmol) with DCM (1 mL) under nitrogen. With stirring, acetyl chloride (12 μL, 0.168 mmol) was added dropwise to a yield a suspension that quickly became a solution. After complete addition of the chloride, triethylamine (32.0 μL, 0.229 mmol) was added in one aliquot. The reaction was diluted with water after 10 minutes and extracted with dichloromethane before drying over sodium sulfate, filtering, and concentrating under reduced pressure to a yellow oil. It was purified by column chromatography (2M NH3/MeOH/DCM). The resulting oil was resolubilized in dichloromethane and flushed through a plug of silica to yield 1-(4-(4-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone as a pale yellow oil. MS (ESI, pos. ion) m/z: 440.2 (M+1). IC50 (uM) ++++.

Workup

  1. customa yield a suspension that
  2. additionwas added in one aliquot
  3. extractionextracted with dichloromethane
  4. dry with materialbefore drying over sodium sulfate
  5. filtrationfiltering
  6. concentrationconcentrating under reduced pressure to a yellow oil
  7. customIt was purified by column chromatography (2M NH3/MeOH/DCM)
  8. customflushed through a plug of silica

Sources & evidence

ORD record
ord-cd44ec22d1f1495698890a422085ac03
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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