Acetic Acid → Ethyl 6-(4-((5-(furo[3,2-c]pyridin-2-yl)-[1,2,4]-oxadiazol-3-yl)methyl)piperidin-1-yl)nicotinate

HRID 217204

Reaction equation

HRID 217204 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[N:12]=[C:11]([C:13]3[O:21][C:20]4[CH:19]=[CH:18][N:17]=[CH:16][C:15]=4[CH:14]=3)[O:10][N:9]=2)[CH2:3][CH2:2]1.Cl[C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:24]=1.C1CCN2C(=NCCC2)CC1.CC(O)=O>CS(C)=O>[O:21]1[C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[CH:14]=[C:13]1[C:11]1[O:10][N:9]=[C:8]([CH2:7][CH:4]2[CH2:5][CH2:6][N:1]([C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:24]=3)[CH2:2][CH2:3]2)[N:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2799611Ethyl 6-chloronicotinateHCID 116305842-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine

Product 1

HCID 57659479Ethyl 6-(4-((5-(furo[3,2-c]pyridin-2-yl)-[1,2,4]-oxadiazol-3-yl)methyl)piperidin-1-yl)nicotinate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(3-Piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine (Preparation 12, 50 mg, 0.176 mmol), ethyl 6-chloronicotinate (49 mg, 0.264 mmol) and DBU (40 mg, 0.264 mmol) were shaken in DMSO (1 mL) at 100° C. for 20 h. The reaction mixture was allowed to cool to room temperature, before being acidified with AcOH. Purification by RP-HPLC yielded the title compound: RT=5.74 min; m/z (ES+)=434.4 [M+H]+.

Workup

  1. customPurification by RP-HPLC

Sources & evidence

ORD record
ord-8e544a8544104284b3ce8ef4f7bf76f9
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Linked notes

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