2-Fluorophenyl isothiocyanate → 5-[(2-Fluorophenyl)amino]-N-[4-(propylsulfonyl)phenyl]-1,3,4-oxadiazole-2-carboxamide
Reaction equation
[NH:1]([C:3](=[O:19])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5])[NH2:2].N(C(=O)C(NC1C=CC([C@H]2CC[C@H](CC(OC)=O)CC2)=CC=1)=O)N.[F:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N:51]=[C:52]=S>>[F:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH:51][C:52]1[O:19][C:3]([C:4]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:11][CH:12]=2)=[O:5])=[N:1][N:2]=1Participants
4
Procedure
Following the general procedure of Example 105 but using 2-hydrazino-2-oxo-N-[4-(propylsulfonyl)phenyl]acetamide (Intermediate 97) as starting material in place of methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]acetate and using 2-fluorophenylisothiocyanate in place of 2-isothiocyanatopyridine the title compound was obtained as a solid; 1H NMR δ 0.90 (t, 3H), 1.46-1.62 (m, 2H), 3.18-3.27 (m, 2H), 7.12-7.20 (m, 1H), 7.22-7.35 (m, 2H), 7.87 (d, 2H), 7.99-8.10 (m, 3H), 10.90 (s, 1H), 11.50 (s, 1H); MS m/e MH+ 405.
Sources & evidence
- ORD record
- ord-a2417397d7714bf5b50c7d2ae01e2585
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795283B2
Reaction notes
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