2-Chloro-5-(chloromethyl)pyridine → 1-(6-Chloro-pyridin-3-ylmethyl)-3-(3-phenoxy-propyl)-1,3-dihydro-benzoimidazol-2-ylideneamine, hydrochloride salt

HRID 410354Notes

Reaction equation

HRID 410354 reaction equation
F[C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[NH:19])=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Cl)=[CH:25][N:24]=1.[Na+].[Br-]>CC(=O)CC>[ClH:22].[Cl:22][C:23]1[N:24]=[CH:25][C:26]([CH2:29][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]3[CH:20]=[CH:21][CH:2]=[CH:3][CH:4]=3)[C:11]2=[NH:19])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 253881Sodium BromideHCID 178509078HCID 178509078, compound

Product 1

HCID 1317316381-(6-Chloro-pyridin-3-ylmethyl)-3-(3-phenoxy-propyl)-1,3-dihydro-benzoimidazol-2-ylideneamine, hydrochloride saltYield 53.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (2.0 g, 7.01 mmol) in 2-butanone (25 ml) at rt was added 2-chloro-5-chloromethyl-pyridine (2.27 g, 14.0 mmol) followed by NaBr (0.715 g, 7.01 mmol). The reaction was heated to 90° C. where it was maintained for 4 d. After this time, the suspension was cooled to rt and filtered. The collected solid was washed with additional 2-butanone and then dried to give 1-(6-chloro-pyridin-3-ylmethyl)-3-(3-phenoxy-propyl)-1,3-dihydro-benzoimidazol-2-ylideneamine, hydrochloride salt (1.6 g, 51%) which was used without further purification. HPLC-MS 411, 413 [M+1]+.

Workup

  1. temperaturewas maintained for 4 d
  2. temperatureAfter this time, the suspension was cooled to rt
  3. filtrationfiltered
  4. washThe collected solid was washed with additional 2-butanone
  5. customdried

Sources & evidence

ORD record
ord-ac36f96b8f4641c29be11e25efcf25ab
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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