Triethylamine → ((2S,5R)-1-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)pyrrolidine-2,5-diyl)dimethanol

HRID 404483

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([N:17]2[C@@H:21]([CH2:22][OH:23])[CH2:20][CH2:19][C@H:18]2[CH2:24][OH:25])[N:3]=1.Cl.[CH:27]12[NH:34][CH:31]([CH2:32][CH2:33]1)[CH2:30][O:29][CH2:28]2.C(N(CC)CC)C>C(O)C>[CH:31]12[N:34]([C:2]3[N:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=4)[N:5]=[C:4]([N:17]4[C@@H:21]([CH2:22][OH:23])[CH2:20][CH2:19][C@H:18]4[CH2:24][OH:25])[N:3]=3)[CH:27]([CH2:33][CH2:32]1)[CH2:28][O:29][CH2:30]2

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of ((2S,5R)-1-(4-chloro-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)pyrrolidine-2,5-diyl)dimethanol (0.91 g, 2.5 mmol), 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (0.37 g, 2.5 mmol) in ethanol (13 mL) was treated with triethylamine (1 mL) and heated in a microwave reactor for 20 minutes at 130° C. The reaction mixture was purified by automated flash chromatography (methanol/chloroform) to provide the title compound as a hard peach colored foam. MS (ES+)=443.2 (M+H)+

Workup

customThe reaction mixture was purified by automated flash chromatography (methanol/chloroform)

Sources & evidence

ORD record: ord-f3f5d48c603d42f0b930208d09982b2a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748421B2

Linked notes

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