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Triethylamine → 1,1-Dimethylethyl 4-[(1,2,3,4,7,8,9,10-octahydro-2,3-dioxopyrido[3,4-f]quinoxaline-9-yl)carbonyl]-1-piperidine carboxylate

HRID 1530854
Notes
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Reaction equation

HRID 1530854 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:29]1[C:38]2[C:37]3[CH2:39][NH:40][CH2:41][CH2:42][C:36]=3[CH:35]=[CH:34][C:33]=2[NH:32][C:31](=[O:43])[C:30]1=[O:44].C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[O:44]=[C:30]1[NH:29][C:38]2[C:37]3[CH2:39][N:40]([C:14]([CH:11]4[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:13][CH2:12]4)=[O:16])[CH2:41][CH2:42][C:36]=3[CH:35]=[CH:34][C:33]=2[NH:32][C:31]1=[O:43]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 212530731,4,7,8,9,10-Hexahydropyrido[3,4-f]quinoxaline-2,3-dione

Product 1

HCID 212530551,1-Dimethylethyl 4-[(1,2,3,4,7,8,9,10-octahydro-2,3-dioxopyrido[3,4-f]quinoxaline-9-yl)carbonyl]-1-piperidine carboxylate
Yield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of N-Boc-4-piperidinecarboxylic acid (158 mg, 0.69 mmol) and carbonyldiimidazole (119 mg, 0.69 mmol) in tetrahydrofuran (3 mL) under a nitrogen atmosphere was reluxed for 15 min. This solution was then added to suspension of the quinoxalinedione from Example 30 (100 mg, 0.46 mmol) in anhydrous dimethylformamide (3 mL). After stirring for 15 min (nitrogen atmosphere), triethylamine (0.96 mL, 0.69 mmol) was added and the reaction was stirred at 70° C. for 19 h. The mixture was concentrated to dryness and the residue triturated with water and collected by filtration. A beige solid (143 mg, 73% yield) was obtained. mp=283-286° C.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated to dryness
  3. customthe residue triturated with water
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d24d97d156dc4a328589930263f30cee
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197771B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes