Acetic Acid → tert-butyl 4-(3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

HRID 2206334Notes

Reaction equation

HRID 2206334 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)=[N:7][C:8]=1[OH:9])=O.N1CCCCC1.C(O)(=O)C.[CH3:34][C:35]1[N:36]=[C:37]([CH3:50])[C:38]2[N:39]([CH:41]=[C:42]([CH2:44][C:45](OCC)=[O:46])[N:43]=2)[CH:40]=1>CCO>[CH3:34][C:35]1[N:36]=[C:37]([CH3:50])[C:38]2[N:39]([CH:41]=[C:42]([C:44]3[C:45](=[O:46])[O:9][C:8]4=[N:7][C:6]([N:10]5[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]5)=[CH:5][CH:4]=[C:3]4[CH:1]=3)[N:43]=2)[CH:40]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 89657132Ethyl 2-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)acetateHCID 178452079Tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 89793976tert-butyl 4-(3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate (225 mg, 0.7 mmol) in 3 mL of EtOH were treated with piperidine (119.2 mg, 1.4 mmol), acetic acid (252 mg, 4.2 mmol) and ethyl 2-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)acetate (196 mg, 0.84 mmol) at room temperature. The reaction mixture was stirred in microwave reactor at 150° C. for 2 hours. The mixture was concentrated, quenched with a saturated NaHCO3 solution and extracted with dichloromethane three times. The combined organic layers were combined and concentrated. The residue was purified on silica gel to provide tert-butyl 4-(3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate after concentration. MS m/z 491 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. customquenched with a saturated NaHCO3 solution
  3. extractionextracted with dichloromethane three times
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-efa7997f74fe47df9e0442ab66b47dcb
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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