Diisopropylethylamine → HCID 46743364, compound

HRID 416894Notes

Reaction equation

Br[CH2:2][CH:3]1[CH2:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>C(Cl)Cl>[CH:3]1([CH2:2][N:26]2[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]2)[CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 35 °C

Procedure

Bromomethylcyclobutane (0.200 g, 1.34 mmol, 1 eq) was suspended in DCM (2 mL). DIPEA (0.59 mL, 3.35 mmol, 2.5 eq) was added dropwise, followed by N-Boc-piperazine (0.550 g, 2.95 mmol, 2.2. eq), and the reaction mixture was stirred at 35° C. for 2 h. The crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1) to give the title compound (0.030 g, 8.8%); 1H-NMR (500 MHz, CDCl3): δ 1.46 (s, 9H, C(CH3)3), 1.64-1.74 (m, 2H), 1.76-1.96 (m, 2H), 2.02-2.12 (m, 2H), 2.37 (t, J=5.0 Hz, 4H, piperazine N(CH2)2), 2.43 (d, J=7.0 Hz, 2H, NCH2), 2.55 (m, 1H, cyclobutyl CH), 3.43 (t, J=5.0 Hz, 4H, piperazine N(CH2)2); GC-MS (Cl, m/z): Rt=3.77 min—255 [(M+H)+, 100%].

Workup

customThe crude product was purified by column chromatography on a Biotage SP1 system (DCM/EtOAc; v/v 1:1)

Sources & evidence

ORD record: ord-ee0f291475c24be69fa2320b81cf5603
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088761B2

Reaction notes

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