Sulfuric Acid → HCID 178461691, compound

HRID 1094330Notes

Reaction equation

HRID 1094330 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([C:17]3[C:18](N)=[N:19][O:20][N:21]=3)[CH3:16])=[CH:11][CH:10]=2)[S:6][CH:7]=1.N([O-])=[O:26].[Na+].OS(O)(=O)=O>CC(O)=O.Cl.O>[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([C:17]3[C:18]([OH:26])=[N:19][O:20][N:21]=3)[CH3:16])=[CH:11][CH:10]=2)[S:6][CH:7]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 86645982HCID 86645982, compound

Product 1

HCID 178461691HCID 178461691, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a cooled solution of 4-[(1R)-1-{4-[(4-(trifluoromethyl)-1,3-thiazol-2-yl)amino]phenyl}ethyl]-1,2,5-oxadiazol-3-amine (0.2 g, 0.56 mmol) in AcOH (5 ml) and 37% HCl (3 ml), a solution of sodium nitrite (44 mg, 0.845 mmol) in water (3 ml) was added dropwise. The resulting reaction mixture was stirred for 30 min, then conc. H2SO4 (0.5 ml) was added and the reaction quenched with a saturated solution of NH4Cl (10 ml); the resulting mixture was extracted with Et2O (3×10 ml) and the collected organic extracts were evaporated under vacuum; the crude was purified by flash chromatography to afford pure 4-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1,2,5-oxadiazol-3-ol (13) (0.17 g, 0.48 mmol) as a white solid (85%). [α]D=−51 (c=1; CH3OH); 1H-NMR (DMSO-d6): δ 8.25 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.05 (s, 1H), 3.90 (q, 1H, J=7 Hz), 1.75 (d, 3H, J=7 Hz).

Workup

  1. customThe resulting reaction mixture
  2. customthe reaction quenched with a saturated solution of NH4Cl (10 ml)
  3. extractionthe resulting mixture was extracted with Et2O (3×10 ml)
  4. customthe collected organic extracts were evaporated under vacuum
  5. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-24476fdc9cd349ae8d622c625cbe650c
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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