Carbon Tetrachloride → HCID 66692180, compound

HRID 1808878Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4]C=1.C1C(=O)N([Cl:28])C(=O)C1.CCOC(C)=O.[C:35]([Cl:39])(Cl)(Cl)Cl>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:5]([Cl:28])=[CH:4][C:35]=1[Cl:39]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of tert-butyl 4-(6-aminopyridin-2-yl)piperazine-1-carboxylate (320 mg, 1.150 mmol) and NCS (307 mg, 2.299 mmol) in Carbon tetrachloride (10 mL)/CH2Cl2 (5.00 mL) was refluxed at 40° C. for 2 h. Purification on silicon gel column with DCM, then 2% EtOAc in DCM gave tert-butyl 4-(6-amino-3,5-dichloropyridin-2-yl)piperazine-1-carboxylate (110 mg, 0.305 mmol, 26.5% yield). 1H-NMR (CDCl3, 500 MHz): δ 7.39 (1H, s), 4.71 (2H, s), 3.53 (4H, m), 3.21 (4H, m), 1.47 (9H, s).

Workup

customPurification on silicon gel column with DCM

Sources & evidence

ORD record: ord-82d029bdadba41aab537231c5719f593
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362004B2

Reaction notes

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