HCID 22220589, compound → HCID 69654744, compound

HRID 1061427Notes

Reaction equation

HRID 1061427 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1[C:34]2[NH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[C:25]([O:35][CH:36]2[O:38][C@H:37]2[CH3:39])=[CH:24][CH:23]=1>CO>[CH2:1]([N:8]([CH:9]1[CH2:10][N:11]([C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[CH2:12]1)[CH2:39][C@H:37]([OH:38])[CH2:36][O:35][C:25]1[C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:33][C:34]=2[CH:22]=[CH:23][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22220589HCID 22220589, compoundHCID 86584414HCID 86584414, compound

Product 1

HCID 69654744HCID 69654744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl-[1-(4-nitro-phenyl)-azetidin-3-yl]-amine (which was obtained in Example 398) (1.95 g, 6.87 mmol) and (2S)-3-(9H-carbazol-4-yloxy)-methyl oxirane (Berridge et al., Int. J. RadiaL Appl. Instrum., 1992, 563) (1.64 g, 6.87 mmol) was stirred at reflux in anhydrous methanol for 24 hours. Methanol was removed in vacuo and the desired product was isolated using silica gel flash chromatography to give 3.01 g of product as a yellow solid; 1H NMR (300 MHz, CDCl3) δ2.90 (m, 2H), 3.04 (s, 1H), 3.85 (m, 3H), 3.98 (m, 3H), 4.23 (m, 3H), 6.01 (d, 2H, J=7.26Hz), 6.61 (d, 1H, J=8.10 Hz), 7.06 (d, 1H, J=8.04 Hz), 7.17 (t, 1H, J=2.14 Hz), 7.34 (m, 7H), 7.97 (d, 2H, J=9.12 Hz), 8.14 (t, 2H, J=8.79 Hz); MS (ES) m/z: 522.9 (MH+); Anal. Calcd. for C31H30N4O4: C, 71.25; H, 5.79; N, 10.72. Found: C, 70.77; H, 6.17; N, 9.61.

Workup

  1. customMethanol was removed in vacuo

Sources & evidence

ORD record
ord-cee421f4bce74e4c81fb88c2efc1e0bb
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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