Hydrochloric Acid → HCID 136368227, compound

HRID 349287Notes

Reaction equation

HRID 349287 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=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]([C:20]2[C:21]([CH:32]=O)=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[N:8]1.[OH2:43].O.O.C([O-])(=O)C.[Na+].[NH2:51]O.Cl>C(Cl)Cl.CO>[F:40][C:37]([F:39])([F:38])[C:35]1[CH:34]=[C:5]([CH:4]=[C:3]([C:2]([F:42])([F:1])[F:41])[CH:36]=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]([C:20]2[C:21]([CH:32]=[N:51][OH:43])=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[N:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10196880HCID 10196880, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 136368227HCID 136368227, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[1-(3,5-Bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carbonyl]-5-(2-chloro-phenyl)-isoxazole-3-carbaldehyde (0.076 g, 0.13 mmol) in CH2Cl2 (2 mL) and MeOH (2 mL), add sodium acetate trihydrate (0.034 g, 0.25 mmol) and hydroxylamine.HCl (0.018 g, 0.25 mmol) and stir at RT. After 1 h., quench with 75% sat. aq. NH4Cl (4 mL), extract with ethyl acetate, and wash with brine. Dry over MgSO4, filter and concentrate under vacuum. Purify by flash chromatography, (EtOAc/Hexane 10%–50%) to give the title compound. MS(ES) 620.1 (M+1), 1H NMR (300 MHz, CDCl3) δ 8.34 (s, 1H), 7.83 (br s, 2H), 7.74–7.16 (m, 9H), 5.50 (s, 2H).

Workup

  1. customquench with 75% sat. aq. NH4Cl (4 mL)
  2. extractionextract with ethyl acetate
  3. washwash with brine
  4. dry with materialDry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customPurify by flash chromatography, (EtOAc/Hexane 10%–50%)

Sources & evidence

ORD record
ord-09f88371e5604cc487c39b99340ac9a6
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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