8-chlorodibenz[b,f][1,4]oxazepin-10(11H)carbonyl chloride → HCID 86748368, compound

HRID 1768781Notes

Reaction equation

HRID 1768781 reaction equation
[F:1][C:2]([F:33])([CH:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=CN=1)[C:3]([NH:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12][C:11]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:10]1=2)=[O:8])=[O:4].FC(F)(C(O)C1[S:42]C=CC=1)C(NN)=O.ClC1C=CC2OC3C=CC=CC=3CN(C(Cl)=O)C=2C=1>>[F:1][C:2]([F:33])([CH:25]([OH:32])[C:26]1[S:42][CH:29]=[CH:30][CH:31]=1)[C:3]([NH:5][NH:6][C:7]([N:9]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12][C:11]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:10]1=2)=[O:8])=[O:4]

Participants

4

Reactant 3

HCID 149759838-chlorodibenz[b,f][1,4]oxazepin-10(11H)carbonyl chlorideHCID 14976003HCID 14976003, compoundHCID 86748367HCID 86748367, compound

Product 1

HCID 86748368HCID 86748368, compound

Procedure

8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[2,2-difluoro-3-hydroxyl-1-oxo-3-(2-thienyl)propyl]hydrazide (27) was prepared in the same manner as 8-chlorodibenz[b,f][1,4]-oxazepine-10(11H)-carboxylic acid, 2-[2,2-difluoro-3-hydroxy-1-oxo-3-(2-pyridinyl)propyl]hydrazide (11), as described above in Example 11, on a 0.9 mmol scale from α,α-difluoro-β-hydroxy-2-thiophenepropanoic acid, hydrazide (26), prepared as described above in Example 26, and 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carbonyl chloride (2), prepared as described above in Example 2, to yield 0.15 g (39%) of product. Analysis calculated for C21H16N3O4SF2Cl. H2O (M.W. 497.91): C, 50.66; H, 3.64; N, 8.44. Found: C, 50.89; H, 3.33; N, 8.24.

Workup

  1. customprepared
  2. customprepared

Sources & evidence

ORD record
ord-ace27ad52787486a8126fa6613037a73
Source dataset
uspto-grants-1995_01
Patent number
US05378840

Reaction notes

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