tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-bromothiazole-4-carbonyl)piperazine-1-carboxylate

HRID 79116Notes

Reaction equation

[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[O:9])[N:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2-bromothiazole-4carboxylic acid (1.31 g, 6.3 mmol) was combined with tert-butyl piperazine-1-carboxylate (1.2 g, 6.3 mmol) in DCM (15 mL), and then stirred at 20° C. until it formed a clear solution. N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.2 g, 6.3 mmol) was then added, and the reaction was stirred at 20° C. for 2 hours. The reaction was concentrated in vacuum, before transferring it to a separation funnel with ethyl acetate. The organic layer was washed with saturated NaHCO3, water, NH4Cl, and then with brine. After drying the organic layer with MgSO4, it was concentrated in vacuum to yield compound 72 (2.2 g, 91%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.16 (1H, s), 3.61 (4H, m), 3.38 (4H, m), 1.42 (9H, s) ppm; LCMS-ESI (POS), M/Z, M+1-C3H9: Found 320.0.

Workup

customformed a clear solution
stirringthe reaction was stirred at 20° C. for 2 hours
concentrationThe reaction was concentrated in vacuum
washThe organic layer was washed with saturated NaHCO3, water, NH4Cl
dry with materialAfter drying the organic layer with MgSO4, it
concentrationwas concentrated in vacuum

Sources & evidence

ORD record: ord-28eac06b7a984ea8950dc23d30f3b495
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841312B2

Reaction notes

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