3-(aminomethyl)-N,N-dimethylaniline → HCID 57919919, compound
Reaction equation
FC1(F)CC1CN1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O.[F:22][C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[C:32](=[O:33])[N:31]([C:34]3[S:35][C:36]([C:40]([OH:42])=O)=[C:37]([CH3:39])[N:38]=3)[CH:30]=[N:29]2)=[CH:25][CH:24]=1.[NH2:45][CH2:46][C:47]1[CH:48]=[C:49]([CH:53]=[CH:54][CH:55]=1)[N:50]([CH3:52])[CH3:51]>>[CH3:51][N:50]([CH3:52])[C:49]1[CH:48]=[C:47]([CH:55]=[CH:54][CH:53]=1)[CH2:46][NH:45][C:40]([C:36]1[S:35][C:34]([N:31]2[C:32](=[O:33])[N:28]([CH2:27][C:26]3[CH:43]=[CH:44][C:23]([F:22])=[CH:24][CH:25]=3)[N:29]=[CH:30]2)=[N:38][C:37]=1[CH3:39])=[O:42]Participants
Reactant 3
Product 1
Procedure
Following the procedure as describe in Example 16, making variations as required to replace 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid to react with 3-(aminomethyl)-N,N-dimethylaniline, the title compound was obtained as a colourless solid in 50% yield: mp 149-151° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.78 (t, J=5.9 Hz, 1H), 8.71 (s, 1H), 7.35 (dd, J=8.5, 5.6 Hz, 1H), 7.15 (d, J=8.9 Hz, 1H), 7.09 (dd, J=7.9, 6.9 Hz, 2H), 6.66 (s, 1H), 6.58 (dd, J=7.7, 7.7 Hz, 2H), 4.96 (s, 2H), 4.35 (d, J=5.8 Hz, 2H), 2.83 (s, 6H); 13C NMR (75 MHz, DMSO-d6) δ163.7, 161.3, 160.5, 151.6, 151.2, 150.9, 150.1, 140.3, 132.7 (d, 3JC-F=11 Hz), 132.4, 130.4 (d, 2JC-F=33 Hz), 129.2, 123.1, 115.9 (d, 1JC-F=86 Hz), 115.6, 111.7, 111.4, 48.2, 43.6, 40.5, 17.3; MS (ES+) m/z 467.16 (M+1).
Sources & evidence
- ORD record
- ord-8f63eebba583482f8ba191860286b415
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049016B2
Reaction notes
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