Sodium Bicarbonate → HCID 178505566, compound

HRID 2116905Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=2)[NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.Cl[C:21]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=1.[C:31]([O-:34])(O)=[O:32].[Na+]>CN1C(=O)CCC1>[F:28][C:27]([F:30])([F:29])[C:31]([OH:34])=[O:32].[Cl:1][C:2]1[N:3]=[C:4]([C:14]2[CH2:15][CH2:16][N:17]([C:21]3[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:18][CH:19]=2)[NH:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-[4-chloro-5-(4-fluoro-phenyl)-1H-imidazol-2-yl]-1,2,3,6-tetrahydro-pyridine from step (c) above, 2-chloro-3-trifluoromethyl-pyridine (125 mg, 0.689 mmol, TCI America) and NaHCO3 (84 mg, 1.0 mmol) in NMP (3 mL) was heated at 180° C. in a microwave synthesizer for 0.5 h. The reaction mixture was cooled to RT and was filtered. The filter cake was washed with NMP (2×2 mL) and the combined filtrates were concentrated in vacuo. The residue was dissolved in DMSO (2 mL) and purified by preparative HPLC [gradient 10-85% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 423 (M+1).

Workup

temperatureThe reaction mixture was cooled to RT
filtrationwas filtered
washThe filter cake was washed with NMP (2×2 mL)
concentrationthe combined filtrates were concentrated in vacuo
dissolutionThe residue was dissolved in DMSO (2 mL)
custompurified by preparative HPLC [gradient 10-85% MeCN (0.1% TFA)/H2O (0.1% TFA)]

Sources & evidence

ORD record: ord-db3893f6d47244d18d946e9dad771e56
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439360B2

Reaction notes

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