Triethylamine → HCID 178423465, compound

HRID 1842501Notes

Reaction equation

HRID 1842501 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:7]=3[N:6]=2)[CH2:2]1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1Cl.CCN(CC)CC>CS(C)=O.C(Cl)Cl.O>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:23])[C:21]=1[N:1]1[CH2:4][CH:3]([C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:7]=3[N:6]=2)[CH2:2]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 37865313,4,5-TrichloropyridineHCID 178423462HCID 178423462, compound

Product 1

HCID 178423465HCID 178423465, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 2-azetidin-3-yl-5-methyl-1H-benzoimidazole (450 mg, 2.4 mmol), 3,4,5-trichloro-pyridine (438 mg, 2.4 mmol) and Et3N (969 mg, 9.6 mmol) in DMSO (20 ml) was heated at 120° C. under microwave for 1.5 h. Then it was diluted with DCM and H2O. The organic layers were concentrated to give the title compound which was purified by column chromatography and followed by preparative HPLC to afford the pure product 2-[1-(3,5-dichloro-pyridin-4-yl)-azetidin-3-yl]-5-methyl-1H-benzoimidazole (800 mg, yield 55%). [M+1] 333. IC50 (uM) 0.21.

Workup

  1. concentrationThe organic layers were concentrated

Sources & evidence

ORD record
ord-4fe1948e8fcd435ba3aadbeb612ea0d5
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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