Pyridine → HCID 10365176, compound

HRID 855556Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[C:8](=[CH:18]\[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)/[C:9]([NH:11][C:12]2[S:13][C:14]([Cl:17])=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl.CCOCC>[Cl:17][C:14]1[S:13][C:12]([NH:11][C:9](=[O:10])/[C:8](/[C:5]2[CH:6]=[N:7][C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:3][CH:4]=2)=[CH:18]/[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[N:16][CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of (E)-2-(6-aminopyridin-3-yl)-N-(5-chlorothiazol-2-yl)-3-cyclopentylacrylamide (EXAMPLE 75, 50 mg, 143 μmol) in anhydrous CH2Cl2 (3 mL) was treated with pyridine (570 μL, 7.1 mmol) and MsCl (170 μL, 2.2 mmol). After stirring for 3 d at 20° C., the reaction mixture was diluted with Et2O (40 mL), before being extracted with 1M NaOH-saturated aqueous NaHCO3 (1:1, 2×15 mL). The combined aqueous extracts were neutralised with 2M HCl, before being extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (1:1 IH-EtOAc) furnished the title compound: RTA=3.73 min; m/z (ES+)=427.2 [M+H]+.

Workup

extractionbefore being extracted with 1M NaOH-saturated aqueous NaHCO3 (1:1, 2×15 mL)
extractionbefore being extracted with EtOAc (2×50 mL)
washThe combined organic extracts were washed with brine (20 mL)
dry with materialbefore being dried (MgSO4)
filtrationFiltration, solvent evaporation, and column chromatography (1:1 IH-EtOAc)

Sources & evidence

ORD record: ord-d13efdbd37784802962b60fe57451c92
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262196B2

Reaction notes

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