2,4-Difluoroaniline → HCID 57829267, compound
Reaction equation
NC1C=CC(C#N)=C(Cl)C=1.CC1(C)C(=O)N(C2C=C(C3C=CC(F)=CC=3)C(C#N)=CC=2)C(=O)N1.Br[C:36]1[CH:66]=[C:65]([F:67])[CH:64]=[CH:63][C:37]=1[CH2:38][N:39]1[C:43]([CH3:45])([CH3:44])[C:42](=[O:46])[N:41]([C:47]2[CH:52]=[C:51]([C:53]3[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=3)[C:50]([C:60]#[N:61])=[CH:49][CH:48]=2)[C:40]1=[O:62].[F:68][C:69]1[CH:74]=[C:73]([F:75])[CH:72]=[CH:71][C:70]=1[NH2:76]>>[F:68][C:69]1[CH:74]=[C:73]([F:75])[CH:72]=[CH:71][C:70]=1[NH:76][C:36]1[CH:66]=[C:65]([F:67])[CH:64]=[CH:63][C:37]=1[CH2:38][N:39]1[C:43]([CH3:45])([CH3:44])[C:42](=[O:46])[N:41]([C:47]2[CH:52]=[C:51]([C:53]3[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=3)[C:50]([C:60]#[N:61])=[CH:49][CH:48]=2)[C:40]1=[O:62]Participants
Procedure
The compound of Example 253 (5-{3-[2-(2,4-difluorophenylamino)-4-fluorobenzyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl}-4′-fluorobiphenyl-2-carbonitrile, molecular weight 558.16 (C31H22F4N4O2); retention time Rt=2.38 min. [B]; MS (ESI): 559.15 (MH+)) was obtained similarly to the manner described for the preparation of the compound of Example 223 via the sequence of 4-amino-2-chlorobenzonitrile→5-amino-4′-fluorobiphenyl-2-carbonitrile (253.3, 1H NMR: 7.54-7.49, m, 3H, 7.31, t, 2H, 6.61, m, 2H, 6.25, s, 2H)→5-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-4′-fluorobiphenyl-2-carbonitrile (253.1, 1H NMR: 8.73, s, 1H; 8.09, d, 1H, 7.74, s, 1H, 7.65, m, 3H, 7.41, m, 2H, 1.42, s, 6H)→5-[3-(2-bromo-4-fluorobenzyl)-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-4′-fluorobiphenyl-2-carbonitrile (253.2, 1H NMR: 8.1, d, 1H, 7.8, s, 1H, 7.75, d, 1H, 7.69-7.59, m, 4H; 7.41, t, 1H, 4.61, s, 2H, 1.4, s, 6H) δ 253 (from 253.2 by reaction with 2,4-difluorophenylamine).
Sources & evidence
- ORD record
- ord-f65a7fd6c7784955b5c6cacafff69aba
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07759366B2
Reaction notes
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