Diisopropylethylamine → HCID 178452336, compound

HRID 2383436Notes

Reaction equation

[Br:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15](=[O:24])[CH:16](Cl)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.CCN(C(C)C)C(C)C.[N:34]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>O1CCOCC1>[Br:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15](=[O:24])[CH:16]([N:37]4[CH2:36][CH2:35][N:34]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38]4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-chloro-2-phenylethanone (0.38 g, 0.94 mmol) in 1,4-dioxane (15 mL) was added Hunig's Base (0.50 mL, 2.82 mmol) and tert-butyl piperazine-1-carboxylate (0.349 g, 1.88 mmol). The reaction mixture was heated at 100° C. for 16 hours. The solvent was removed under reduced pressure and the crude product was purified using (SiO2, gradient from 80% EtOAc in hexanes to 100% EtOAc in hexane) to give the desired product, tert-butyl 4-(2-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethyl)piperazine-1-carboxylate as a white solid (0.188 g, 41%). M.p.=159-161° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.95 (s, 1H), 8.41 (s, 1H), 7.46-7.2 (m, 5H), 5.07-4.65 (m, 3H), 4.0-3.7 (m, 2H), 3.3-3.1 (m, 5H), 2.95-2.85 (m, 1H), 2.53-2.3 (m, 4H), 1.35 (s, 9H); LCMS [M+H]: 555.

Workup

customThe solvent was removed under reduced pressure
customthe crude product was purified

Sources & evidence

ORD record: ord-fd5acfb7af434ffd89908350bbe48f34
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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