Reaction equation
O=C(NN[C:13]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][C:17]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]1=2)=[O:14])CCC1C=CC=CN=1.[F:31][C:32]([F:45])([CH:37]([OH:44])[C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)[C:33]([NH:35][NH2:36])=[O:34].ClC1C=CC2OC3C=CC=CC=3CN(C(Cl)=O)C=2C=1>C(O)(=O)C.Cl>[F:45][C:32]([F:31])([CH:37]([OH:44])[C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)[C:33]([NH:35][NH:36][C:13]([N:15]1[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][C:17]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:16]1=2)=[O:14])=[O:34]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
The free base of 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[2,2-difluoro-3-hydroxy-1-oxo-3-(4-pyridinyl)propyl]hydrazide (51) was prepared in the same manner as 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(2-pyridinyl)propyl]hydrazide (6), as described above in Example 6, on a 1.75 mmol scale from α,α-difluoro-β-hydroxy-3-(4-pyridinyl)-propanoic acid, hydrazide (50), prepared in the manner described above in Example 50, and 8-chlorodibenz[b,f][1,4]-oxazepine-10(11H)-carbonyl chloride (2), prepared in the manner described above in Example 2, for a yield of 0.098 g (12%) of product. The free base was taken up in acetic acid (1.5 mL) and 1M HCl (1.5 mL). The material was lyophilized to yield 0.049 mg of the hydrochloride salt. Analysis calculated for C22H17N4O4F2Cl.HCl. 0.25 H2O (M.W. 514.83): C, 51.23; H, 3.62; N, 10.86. Found: C, 50.85; H, 3.67; N, 10.94.
Workup
- customprepared in the manner
- customprepared in the manner
Sources & evidence
- ORD record
- ord-21191f15cdc64761a0c3dde1495f0497
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576315
Linked notes
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