Hydroxyamine hydrochloride → HCID 86601251, compound

HRID 2252002Notes

Reaction equation

HRID 2252002 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH2:24][OH:25])[C:19]=2[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=O)[N:9]=[N:8]1.Cl.[NH2:45][OH:46]>N1C=CC=CC=1>[F:42][C:2]([F:43])([F:1])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:40])([F:39])[F:41])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]2[O:22][N:21]=[C:20]([CH2:23][CH2:24][OH:25])[C:19]=2[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=[N:45][OH:46])[N:9]=[N:8]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86601252HCID 86601252, compound

Product 1

HCID 86601251HCID 86601251, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of [5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-3-(2-hydroxy-ethyl)-isoxazol-4-yl]-(2-chloro-phenyl)-methanone (1 eq) in pyridine. Add hydroxylamine HCl (10 eq) and reflux and stir overnight. Quench with H2O, extract with ethyl acetate, and concentrate. Remove remaining pyridine by azeotrope with heptane (2×) in vacuo. Dissolve in CH2Cl2, dry over MgSO4, filter and concentrate under vacuum. Purify by radial chromatography on silica gel to give the title compound. MS (IS) 635.96 (M+1), 1H NMR (CD3Cl): δ 9.59 (br s, 1H), 7.76 (s, 1H), 7.49-6.90 (m, 11H), 5.34 (s, 2H), 3.94 (t, J=5.6 Hz, 2H), 3.07 (t, J=5.6 Hz, 2H).

Workup

  1. customQuench with H2O
  2. extractionextract with ethyl acetate
  3. concentrationconcentrate
  4. customRemove
  5. dissolutionDissolve in CH2Cl2
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. customPurify by radial chromatography on silica gel

Sources & evidence

ORD record
ord-6e0249e9f01d4ee9917322187793b6a3
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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