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1,2-Diaminocyclohexane, trans- → 4-(6-Methoxy-[1,5]naphthyridin-4-yl)-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

HRID 1511797
Notes
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Reaction equation

HRID 1511797 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N.Br[C:32]1[CH:33]=[CH:34][N:35]=[C:36]2[C:41]=1[N:40]=[C:39]([O:42][CH3:43])[CH:38]=[CH:37]2>[Cu]I.O1CCOCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:42][CH3:43])[N:40]=3)[N:35]=[CH:34][CH:33]=2)[C:10](=[O:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 534216178-Bromo-2-methoxy-1,5-naphthyridine

Product 1

HCID 669547734-(6-Methoxy-[1,5]naphthyridin-4-yl)-3-oxo-piperazine-1-carboxylic acid tert-butyl esterYield 12%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A glass vial was charged with 1-Boc-3-oxo-piperazine (commercial; 503 mg, 2.5 mmol), CuI (40 mg, 0.21 mmol) and K3PO4 (888 mg, 4.2 mmol), evacuated and backfilled with argon. Trans-1,2-diaminocyclohexane (24 mg, 0.21 mmol), 8-bromo-2-methoxy-[1,5]naphthyridine (500 mg, 2.1 mmol) and dioxane (2 mL) were added under a flow of argon. The tube was sealed and the mixture was heated at 110° C. for 18 h. The resulting suspension was filtered through a pad of SiO2 (EA). The filtrate was concentrated under reduced pressure and the residue was chromatographed over SiO2 (DCM-MeOH—NH4OH 1000-50-4) to afford the title intermediate as a pale yellow oil (87 mg, 12%).

Workup

  1. customevacuated
  2. customThe tube was sealed
  3. filtrationThe resulting suspension was filtered through a pad of SiO2 (EA)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed over SiO2 (DCM-MeOH—NH4OH 1000-50-4)

Sources & evidence

ORD record
ord-c1841c6fb3434a12a61f4471cc5f1965
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08217029B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes