Dichloromethane → HCID 178477896, compound

HRID 1842513Notes

Reaction equation

HRID 1842513 reaction equation
Cl.Cl.[NH:3]1[CH2:6][CH:5]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:9]=3[N:8]=2)[CH2:4]1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[C:21]([Cl:25])=[CH:20][N:19]=1.C(N(CC)CC)C.ClCCl>O1CCOCC1.O>[Cl:16][C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:7]([CH:5]3[CH2:6][N:3]([C:20]4[C:21]([Cl:25])=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=4)[CH2:4]3)=[N:8][C:9]=2[CH:15]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 178478572HCID 178478572, compound

Product 1

HCID 178477896HCID 178477896, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(Azetidin-3-yl)-5-chloro-1H-benzo[d]imidazole dihydrochloride, as prepared in preparation 5, (0.16 g, 0.57 mmol) was added to a solution of 2,4,5-trichloropyrimidine (0.11 g, 0.57 mmol) and triethylamine (0.28 mL, 2.00 mmol) in dioxane (2 mL) under argon. The mixture was stirred for 2 h at RT, then dichloromethane and water were added. The resulting layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 5-chloro-2-(1-(2,5-dichloropyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.18 g, 0.51 mmol, 89% yield) as a white solid.

Workup

  1. customThe resulting layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil that
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-a83099e132ba4156acdbd658642d01c5
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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