rel-(2R,6S)-2,6-dimethylpiperazine → HCID 66919131, compound

HRID 2354180Notes

Reaction equation

HRID 2354180 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[CH:9]1([NH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([CH3:34])=[C:19]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[C:27](F)[CH:26]=[CH:25][C:24]=3[N+:30]([O-:32])=[O:31])[CH:20]=2)=[O:14])[CH2:11][CH2:10]1>>[CH:9]1([NH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([CH3:34])=[C:19]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[C:27]([N:6]4[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]4)[CH:26]=[CH:25][C:24]=3[N+:30]([O-:32])=[O:31])[CH:20]=2)=[O:14])[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 669189745-fluoro-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-nitrobenzamide

Product 1

HCID 66919131HCID 66919131, compound

Procedure

Using an analogous procedure to that described paragraph (A) in the portion of Example 13 which is concerned with the preparation of starting materials cis-2,6 dimethylpiperazine was reacted with N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-fluoro-2-nitrobenzamide to give N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-nitrobenzamide; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 1.03 (d, 6H), 2.28 (s, 3H), 2.40 (t, 2H), 2.79 (m, 3H), 3.94 (d, 2H), 7.05 (m, 2H), 7.28 (d, 1H), 7.55 (d, 1H), 8.01 (m, 2H), 8.36 (s, 1H), 9.87 (s, 1H); Mass Spectrum: M+H+ 452.

Sources & evidence

ORD record
ord-f1e8730f11c5455b9e9594c359fdc025
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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