Triethylamine → t-Butyl(S,S)-5-(6-Phenyl-pyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 657721Notes

Reaction equation

C(N(CC)CC)C.[C@H:8]12[CH2:14][C@H:11]([NH:12][CH2:13]1)[CH2:10][N:9]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].Cl[C:23]1[N:24]=[N:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][CH:28]=1>C1(C)C=CC=CC=1>[C:29]1([C:26]2[N:25]=[N:24][C:23]([N:12]3[CH2:13][C@@H:8]4[CH2:14][C@H:11]3[CH2:10][N:9]4[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:28][CH:27]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Triethylamine (20 mL) was added to a suspension of t-butyl (S,S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (3.43 g, 17.3 mmol, Aldrich Chemical Company) and 3-chloro-6-phenylpyridazine (3.30 g. 17.3 mmol, Aldrich Chemical Company) in toluene (50 mL) and the mixture was heated under nitrogen at 100° C. for 7 days. The dark mixture was cooled to room temperature, and the resulting precipitate was isolated by filtration, washed with toluene (15 mL) and dried under vacuum to provide the title compound as an off-white solid (3.00 g). The filtrate was concentrated and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate, to provide additional product (0.41 g, total yield 3.41 g, 56%); MS (DCI/NH3) m/z 353 (M+H)+.

Workup

temperatureThe dark mixture was cooled to room temperature
customthe resulting precipitate was isolated by filtration
washwashed with toluene (15 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-41c32f0d675548dc9df94a517cc1085b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076350B2

Reaction notes

Loading…