Triethylamine → HCID 86696453, compound

HRID 870746Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[N:7]([CH3:13])[CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[N:20]2[N:21]=[C:22](F)[CH:23]=[CH:24][C:19]2=[N:18][CH:17]=1.C(N(CC)CC)C>C(O)(C)C>[C:1]([O:5][C:6](=[O:14])[N:7]([CH:8]1[CH2:12][CH2:11][N:10]([C:22]2[CH:23]=[CH:24][C:19]3[N:20]([C:16]([Br:15])=[CH:17][N:18]=3)[N:21]=2)[CH2:9]1)[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (1.2 g, 6 mmol), 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (648 mg, 3 mmol), and triethylamine (1.67 ml, 12 mmol) in isopropyl alcohol (3 ml) was heated in a microwave at 140° C. for 20 min. The reaction mixture was allowed to stand for overnight and the white solid was collected by filtration and washed with MeOH to give the titled compound (750 mg). The filtrate was concentrated and the residue was subjected to ISCO (40 g column), to give further titled compound (360 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45-1.52 (m, 9H) 2.03-2.27 (m, 2H) 2.83 (s, 3H) 3.39-3.54 (m, 2H) 3.69-3.77 (m, 2H) 6.58 (d, J=9.92 Hz, 1H) 7.49 (s, 1H) 7.65 (d, J=9.70 Hz, 1H). LRMS (ESI) m/z 396.1 and 398 [(M+H)]+, calc'd for C16H22BrN6O2: 396.29.

Workup

filtrationthe white solid was collected by filtration
washwashed with MeOH

Sources & evidence

ORD record: ord-93bf9ad10cb84a67b1725a7b5228b86c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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