Acetic Acid → t-butyl 4-(3-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)piperazine-1-carboxylate

HRID 2206325Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:7][C:8]=1[OH:9])=O.[CH3:23][C:24]1[CH:29]=[CH:28][N:27]2[CH:30]=[C:31]([CH2:33][C:34](OCC)=[O:35])[N:32]=[C:26]2[CH:25]=1.N1CCCCC1.C(O)(=O)C>CCO.O>[CH3:23][C:24]1[CH:29]=[CH:28][N:27]2[CH:30]=[C:31]([C:33]3[C:34](=[O:35])[O:9][C:8]4=[N:7][C:6]([N:10]5[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]5)=[CH:5][CH:4]=[C:3]4[CH:1]=3)[N:32]=[C:26]2[CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of t-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)piperazine-1-carboxylate (120 mg, 0.4 mmol) and ethyl 2-(7-methylimidazo[1,2-a]pyridin-2-yl)acetate (96 mg, 0.44 mmol) in EtOH (0.2 mL) were added piperidine (0.3 mL) and acetic acid (0.1 mL). The reaction mixture was heated to 120° C. for 15 hours, and cooled to room temperature. To the mixture was added water (6 mL) to give a precipitate. The precipitate was filtered and washed with water and then ether. After drying under nitrogen, 112 mg (60%) of t-butyl 4-(3-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)piperazine-1-carboxylate was obtained as a yellow solid. MS m/z 462.4 [M+H]+.

Workup

temperaturecooled to room temperature
customto give a precipitate
filtrationThe precipitate was filtered
washwashed with water
customAfter drying under nitrogen

Sources & evidence

ORD record: ord-07b08d47d9814875bd1abb26f499c29c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371336B2

Reaction notes

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