Hydroxyamine hydrochloride → N-(3-{[(9-(hydroxyimino)-7-{[(3-hydroxyphenyl)amino]sulfonyl}-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

HRID 2120917Notes

Reaction equation

HRID 2120917 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[C:23]3[C:15]([C:16]4[CH:17]=[CH:18][C:19]([S:26]([NH:29][C:30]5[CH:31]=[C:32]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[CH:34][CH:35]=5)(=[O:28])=[O:27])=[CH:20][C:21]=4[C:22]3=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:41][OH:42]>N1C=CC=CC=1>[OH:42][N:41]=[C:22]1[C:21]2[CH:20]=[C:19]([S:26]([NH:29][C:30]3[CH:31]=[C:32]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[CH:34][CH:35]=3)(=[O:27])=[O:28])[CH:18]=[CH:17][C:16]=2[C:15]2[C:23]1=[CH:24][C:12]([S:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)(=[O:11])=[O:10])=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

Product 1

HCID 85117338N-(3-{[(9-(hydroxyimino)-7-{[(3-hydroxyphenyl)amino]sulfonyl}-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamideYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 6A (223 mg, 0.396 mmol) in pyridine (3 mL) was treated with hydroxylamine hydrochloride (30 mg, 0.435 mmol) and heated at reflux. After 30 minutes, the mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and H2O. The separated organic phase was washed with 1 N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (75% ethyl acetate/hexanes) to provide the title compound as a light yellow solid (91 mg, 40% yield). 1H NMR (300 MHz, DMSO-d6) δ 13.32 (bs, 1H), 10.2-10.4 (bs, 2H), 9.89 (s, 1H), 9.43 (d, 1H), 8.75 (m, 1H), 8.03-8.17 (m, 3H), 7.8-7.95 (m, 2H), 7.45 (m, 1H), 7.25 (m, 1H), 7.1 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.58 (m, 1H), 6.52 (m, 1H), 6.4 (m, 1H), 1.98 (s, 3H); MS (ESI) 577 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. custompartitioned between ethyl acetate and H2O
  4. washThe separated organic phase was washed with 1 N HCl, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9928e015f54e4c43a8b3419b2a78537f
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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