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 → 1,4,7,8,9,10-Hexahydro-9-(4-piperidinyl carbonyl)pyrido[3,4-f]quinoxaline-2,3-dione

HRID 1106441Notes

Reaction equation

HRID 1106441 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:9]3[CH2:12][N:13]([C:16]([CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[O:17])[CH2:14][CH2:15][C:8]=3[CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:31]>FC(F)(F)C(O)=O>[NH:21]1[CH2:22][CH2:23][CH:18]([C:16]([N:13]2[CH2:14][CH2:15][C:8]3[CH:7]=[CH:6][C:5]4[NH:4][C:3](=[O:31])[C:2](=[O:1])[NH:11][C:10]=4[C:9]=3[CH2:12]2)=[O:17])[CH2:19][CH2:20]1

Participants

3

Reactant 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

Product 1

HCID 212530561,4,7,8,9,10-Hexahydro-9-(4-piperidinyl carbonyl)pyrido[3,4-f]quinoxaline-2,3-dioneYield 101.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of the N-Boc quinoxalinedione from Example 32 (18 mg, 0.042 mmol) in trifluoroacetic acid (1.5 mL) was stirred under a nitrogen atmosphere for 15 min. After concentrating to dryness, the residue was triturated with water, basified to pH 8 and filtered. The filtrate was evaporated to give a beige solid (14 mg, 99% yield).

Workup

  1. concentrationAfter concentrating to dryness
  2. customthe residue was triturated with water
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-1bdfbcbff65b4290a83c522159077865
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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