Ethanesulfonyl chloride → HCID 178477703, compound

HRID 518625Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][O:9][C:10]2[N:15]=[CH:14][C:13]3[NH:16]/[C:17](=[N:25]\[C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)/[N:18]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:12]=3[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:34]([S:36](Cl)(=[O:38])=[O:37])[CH3:35]>CN(C=O)C.O.C(Cl)Cl>[CH2:34]([S:36]([N:22]1[CH2:21][CH2:20][CH:19]([N:18]2[C:12]3[CH:11]=[C:10]([O:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[N:15]=[CH:14][C:13]=3[NH:16]/[C:17]/2=[N:25]\[C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:23]1)(=[O:38])=[O:37])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of (E)-N-(6-(2-(piperidin-1-yl)ethoxy)-1-(piperidin-4-yl)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (0.10 g, 0.223 mmol) in DMF (1.12 mL) was cooled to 0° C. under nitrogen atmosphere. To this mixture was added TEA (0.045 g, 0.446 mmol) followed by ethanesulfonyl chloride (0.043 g, 0.334 mmol). The resulting mixture was stirred for 30 minutes and diluted with water (10 mL) and DCM (20 mL). The organic layer was collected and concentrated to yield a brown residue. The residue was purified by HPLC (10-70% ACN/H2O; 0.1% TFA) to afford (E)-N-(1-(1-(ethylsulfonyl)piperidin-4-yl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide as an off-white solid (15 mg, 12.4%). MS m/z=541.2 [M+H]. Calc'd for C27H36N6O4S: 540.3.

Workup

customThe organic layer was collected
concentrationconcentrated
customto yield a brown residue
customThe residue was purified by HPLC (10-70% ACN/H2O; 0.1% TFA)

Sources & evidence

ORD record: ord-6b5717d0907c4bc18325b51efc63a3ce
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

Loading…