Hydrochloric Acid → 1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutylamine

HRID 872356Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([C:26]5[C:27]([O:32][CH2:33][C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)=[N:28][CH:29]=[CH:30][CH:31]=5)=[CH:22][N:21]4[C:40]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl>C(Cl)Cl.CO>[CH2:33]([O:32][C:27]1[C:26]([C:23]2[CH:24]=[CH:25][C:20]3[N:21]([C:40]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH2:7])[CH2:9][CH2:10][CH2:11]5)=[CH:13][CH:14]=4)[N:19]=3)[CH:22]=2)=[CH:31][CH:30]=[CH:29][N:28]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The crude product from Step 2 (240 mg) was dissolved in DCM/MeOH (1.2 mL/0.76 mL), cooled to 0° C. and treated with HCl (4 M soln in dioxane, 0.94 mL). The reaction was warmed to rt and stirred for 2 hours. The reaction was poured onto ice and extracted with DCM (3×). The organic phase was washed with brine, dried and concentrated in vacuo to give the crude title compound.

Workup

temperatureThe reaction was warmed to rt
additionThe reaction was poured onto ice
extractionextracted with DCM (3×)
washThe organic phase was washed with brine
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4e765f88351f484183ce7050a90ffb92
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Reaction notes

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