Morpholine → HCID 18422114, compound

HRID 1281724Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[C:12]([NH:14][C:15]2[CH:16]=[C:17]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27](Cl)[N:26]=3)=[O:24])[CH:18]=[CH:19][C:20]=2[CH3:21])=[O:13])[CH2:4][CH2:3]1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[C:12]([NH:14][C:15]2[CH:16]=[C:17]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[N:26]=3)=[O:24])[CH:18]=[CH:19][C:20]=2[CH3:21])=[O:13])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-{3-[3-(4-methylpiperazin-1-ylmethyl)benzamido]-4-methylphenyl}-6-chloropyridine-2-carboxamide (0.2 g) and morpholine (3 ml) was stirred and heated to 110° C. for 16 hours. The resultant solution was cooled to ambient temperature and poured into water and extracted with methylene chloride. The organic phase was evaporated and the residue was purified by reversed-phase column chromatography on a C18 isolute column eluting initially with water and then with a 5:1 mixture of water and methanol. There was thus obtained the title compound (0.169 g); NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.19 (s, 3H), 2.25-2.39 (m, 8H), 3.52 (s, 2H), 3.57-3.6 (m, 4H), 3.71-3.75 (m, 4H), 7.05 (d, 1H), 7.22 (d, 1H), 7.4-7.49 (m, 3H), 7.64 (d, 1H), 7.76 (t, 1H), 7.82-7.88 (m, 3H), 9.92 (s, 1H), 10.08 (s, 1H); Mass Spectrum: M+H+ 529.

Workup

extractionextracted with methylene chloride
customThe organic phase was evaporated
customthe residue was purified by reversed-phase column chromatography on a C18 isolute column
washeluting initially with water
additionwith a 5:1 mixture of water and methanol

Sources & evidence

ORD record: ord-8079ba4644ec4c9a8494c111036eed9a
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455520B1

Reaction notes

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