Triethylamine → HCID 178477893, compound

HRID 1842491Notes

Reaction equation

HRID 1842491 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[CH:11][N:10]=1.Cl.Cl.[NH:18]1[CH2:21][CH:20]([C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:24]=3[N:23]=2)[CH2:19]1.C(OCC)(=O)C>O1CCOCC1.O>[Cl:31][C:29]1[CH:28]=[CH:27][C:25]2[NH:26][C:22]([CH:20]3[CH2:19][N:18]([C:13]4[CH:12]=[CH:11][N:10]=[C:9]([Cl:8])[N:14]=4)[CH2:21]3)=[N:23][C:24]=2[CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 775312,4-DichloropyrimidineHCID 178478572HCID 178478572, compound

Product 1

HCID 178477893HCID 178477893, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of triethylamine (0.17 mL, 1.25 mmol), 2,4-dichloropyrimidine (0.053 g, 0.36 mmol), and 2-(azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride, as prepared in preparation 5, (0.10 g, 0.36 mmol) in dioxane (1.25 mL) was stirred under argon atmosphere for 3 h at RT. Ethyl acetate and water were added, the resulting layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography to give 5-chloro-2-(1-(2-chloropyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.069 g, 0.22 mmol, 61% yield).

Workup

  1. customthe resulting layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d74876217220477389c8394d8dcb0e0e
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

Loading…