Water → HCID 178477900, compound

HRID 1842514Notes

Reaction equation

HRID 1842514 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:28]=[CH:27][C:11]2[NH:12][C:13]([CH:15]3[CH2:18][N:17]([C:19]4[C:24]([Cl:25])=[CH:23][N:22]=[C:21](Cl)[N:20]=4)[CH2:16]3)=[N:14][C:10]=2[CH:9]=1.ClCCl.O>O1CCOCC1>[Cl:25][C:24]1[C:19]([N:17]2[CH2:18][CH:15]([C:13]3[NH:12][C:11]4[CH:27]=[CH:28][C:8]([Cl:7])=[CH:9][C:10]=4[N:14]=3)[CH2:16]2)=[N:20][C:21]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[N:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 8083MorpholineHCID 178477896HCID 178477896, compound

Product 1

HCID 178477900HCID 178477900, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of morpholine (0.062 mL, 0.711 mmol) and 5-chloro-2-(1-(2,5-dichloropyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole (0.063 g, 0.18 mmol) in dioxane (1 mL) was heated to 60° C. under argon and stirred for 6 h. The mixture was cooled to RT, dichloromethane and water were added, and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 4-(5-Chloro-4-(3-(5-chloro-1H-benzo[d]imidazol-2-yl)azetidin-1-yl)pyrimidin-2-yl)morpholine (0.052 g, 0.13 mmol, 72%) as a white solid. [M+1] 405. IC50 (uM) 0.1554.

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe layers were separated
  3. dry with materialThe organic layer was 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-d518342b9f564b0bb0dcbebb50a1ebbb
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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