N-Hydroxyacetamidine → HCID 59485952, compound
Reaction equation
O1C=NC=N1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C@@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[C@H:16]([CH2:26][N:27]3[CH:31]=[C:30]([C:32](O)=[O:33])[N:29]=[N:28]3)[O:15][C:14]2=[O:35])=[CH:9][CH:8]=1.[C:36](=[N:39]O)([NH2:38])[CH3:37]>O1CCOCC1.C(#N)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C@@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[C@H:16]([CH2:26][N:27]3[CH:31]=[C:30]([C:32]4[O:33][N:39]=[C:36]([CH3:37])[N:38]=4)[N:29]=[N:28]3)[O:15][C:14]2=[O:35])=[CH:11][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Reference for 1,2,4-oxadiazole formation: Bioorg. Med. Chem. Lett. 1999, 9, 209. A solution of 1-(((4S,5S)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl)-1H-1,2,3-triazole-4-carboxylic acid (32 mg, 0.07 mmol) in dioxane (0.5 mL) is treated with N,N′-carbonyldiimidazole and stirred at room temperature for 30 min. Acetamide oxime (10 mg, 0.13 mmol) is then added and the mixture stirred for 2 h at room temperature then at 100° C. for 18 h. The reaction solution is then diluted with acetonitrile and filtered through a Whatman 0.42 μM and purified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)) HPLC to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 8.93 (s, 1H), 7.47-7.44 (m, 2H), 7.33-7.28 (m, 3H), 7.05-7.00 (m, 2H), 6.88 (ddd, J=7.9, 2.5, 0.8 Hz, 1H), 5.62 (d, J=5.0 Hz, 1H), 5.25-5.24 (m, 2H), 5.03 (ddd, J=5.7, 5.5, 4.9 Hz, 1H) 3.76 (s, 3H), 2.40 (s, 3H); HPLC-MS calculated C22H19ClN6O4 (M+H+) 467.1, found 467.1.1.
Workup
- stirringthe mixture stirred for 2 h at room temperature
- waitat 100° C. for 18 h
- filtrationfiltered through a Whatman 0.42 μM
- custompurified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)) HPLC
Sources & evidence
- ORD record
- ord-8a6f1a2804124d46912ea18e1cec06f4
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431607B2
Reaction notes
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