Morpholine → HCID 59463546, compound

HRID 1713149Notes

Reaction equation

HRID 1713149 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[CH:19]=[C:18](Cl)[N:17]=[N:16][C:15]=4[CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:24])[CH2:12][N:13]3[CH2:22][CH2:21][C:20]4[CH:19]=[C:18]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[N:17]=[N:16][C:15]=4[CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59463564HCID 59463564, compound

Product 1

HCID 59463546HCID 59463546, compound

Procedure

A solution of 7-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-3-chloro-5,6,7,8-tetrahydropyrido[3,4-c]pyridazine (0.2 g) in morpholine (5 ml) is heated at 200° C. in a microwave for 2 hr. The excess morpholine is removed in vacuo. The crude mixture is purified by PTLC (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 6.60 (1H, s), 3.86 (2H, s), 3.82 (4H, t), 3.50-3.70 (8H, m), 3.40 (2H, s), 2.62-2.84 (5H, m), 2.24-2.32 (4H, m), 1.60-2.06 (6H, m); MS (+VE) m/z 401.2 (M++1).

Workup

  1. customThe excess morpholine is removed in vacuo
  2. customThe crude mixture is purified by PTLC (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-19c33097fd2e40f7aeb40cc36e7f8c7a
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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