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

HRID 707190Notes

Reaction equation

HRID 707190 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[O:34][CH:31]([CH2:32][CH2:33]1)[CH2:30][NH:29][CH2:28]2.C(N(CC)CC)C>C(O)C>[CH:31]12[O:34][CH:27]([CH2:33][CH2:32]1)[CH2:28][N:29]([C:2]1[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)[N:5]=[C:4]([N:17]3[C@@H:21]([CH2:22][OH:23])[CH2:20][CH2:19][C@H:18]3[CH2:24][OH:25])[N:3]=1)[CH2:30]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochlorideHCID 86636521((2S,5R)-1-(4-chloro-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)pyrrolidine-2,5-diyl)dimethanol

Product 1

HCID 67022148((2S,5R)-1-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)pyrrolidine-2,5-diyl)dimethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of ((2S,5R)-1-(4-chloro-6-(4-nitrophenyl)-1,3,5-triazin-2-yl)pyrrolidine-2,5-diyl)dimethanol (1.3 g, 2.7 mmol), 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.51 g, 3.4 mmol) in ethanol (15 mL) was treated with triethylamine (1.35 mL, 10 mmol) and heated with a heat gun briefly to reflux. 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

  1. temperatureheated with a heat gun briefly
  2. temperatureto reflux
  3. customThe reaction mixture was purified by automated flash chromatography (methanol/chloroform)

Sources & evidence

ORD record
ord-f602fec253c84ca9a28a5d84eeb20404
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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