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

HRID 2206330Notes

Reaction equation

[CH:1]([C:3]1[C:4]([OH:22])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)=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:22][C:4]4[CH:5]=[C:6]([N:9]5[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:13][CH2:14]5)[N:7]=[CH:8][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-4-hydroxypyridin-2-yl)piperazine-1-carboxylate (124 mg, 0.40 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 (2 mL) to give a precipitate. The precipitate was filtered and washed with water and then ether. After drying under nitrogen, 115 mg (63%) of t-butyl 4-(3-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-oxo-2H-pyrano[3,2-c]pyridin-7-yl)piperazine-1-carboxylate was obtained as a yellow solid. MS m/z 462.3 [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-4ea86c5b30094ef6b646548fdec8f427
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371336B2

Reaction notes

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