Di-tert-butyl dicarbonate → HCID 89922751, compound

HRID 921873Notes

Reaction equation

HRID 921873 reaction equation
[Cl:1][C:2]1[C:9]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]2=[O:16])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:17]([O-])=O.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>C1COCC1.C(Cl)Cl>[NH2:17][C:3]1[C:2]([Cl:1])=[C:9]([N:10]2[CH2:15][CH2:14][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:12][C:11]2=[O:16])[CH:8]=[C:5]([C:6]#[N:7])[CH:4]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 899230564-Chloro-3-nitro-5-(2-oxo-1-piperazinyl)benzonitrile

Product 1

HCID 89922751HCID 89922751, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

This amine was dissolved in THF (2.000 mL) and DCM (2.000 mL), then TEA (0.030 mL, 0.214 mmol) was added followed by BOC2O (0.033 mL, 0.143 mmol). After stirring at room temperature for 2 h, LC-MS indicated completion, it was concentrated and purification via flash chromatography (0-10% MeOH in DCM, 12 g) gave tert-butyl 4-(3-amino-2-chloro-5-cyanophenyl)-3-oxopiperazine-1-carboxylate (20 mg) as an off-white solid.

Workup

  1. concentrationwas concentrated
  2. custompurification via flash chromatography (0-10% MeOH in DCM, 12 g)

Sources & evidence

ORD record
ord-fff37c42760f4f448ad24c2a24e7af2a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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