Potassium Carbonate → 3-(Cyclopropylmethyl)-7-(4-phenyl-1-piperidinyl)-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

HRID 587658Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of compound D5 (0.2 g, 0.86 mmol), 4-phenylpiperidine (0.166 g, 1.031 mmol), K2CO3 (0.148 g, 1.074 mmol) in CH3CN (5 ml) was heated in a sealed tube at 150° C. under microwave irradiation for 5 min. The mixture was then cooled to r.t. and the solvents evaporated in vacuo. The residue thus obtained was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent). The desired fractions were collected and concentrated in vacuo to yield compound E13 as yellow solid (0.150 g, 49%).

Workup

temperatureThe mixture was then cooled to r.t.
customthe solvents evaporated in vacuo
customThe residue thus obtained
customwas purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 3% as eluent)
customThe desired fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0066d027aa5c4c349377616be7c3a624
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226930B2

Reaction notes

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