Triethylamine → HCID 86614615, compound

HRID 564329Notes

Reaction equation

HRID 564329 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([C@@:12]23[CH2:27][CH2:26][C:25](=O)[CH2:24][C@H:13]2[CH2:14][O:15][C:16]2[C:21]3=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH3:32][O:33][NH2:34].CCN(CC)CC>CCO>[CH3:32][O:33][N:34]=[C:25]1[CH2:24][CH:13]2[CH2:14][O:15][C:16]3[C:21]([C:12]2([S:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:29])([F:1])[F:30])=[CH:8][CH:7]=2)(=[O:10])=[O:11])[CH2:27][CH2:26]1)=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[F:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67007038HCID 67007038, compound

Product 1

HCID 86614615HCID 86614615, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-10a-(4-trifluoromethyl-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one (40 mg, 0.10 mmol) in EtOH (2 mL) was added O-methyl hydroxylamine hydrochloride (20 mg, 0.23 mmol), and NEt3 (20 uL, 0.14 mmol). The reaction mixture was stirred overnight and then PS-dimethylaminoethyl resin was added, the stirring was continued for 2 h and then the resin removed by filtration. The solvent was removed under a stream of N2 and the residue purified by preparative TLC eluting with 25% ethyl acetate in hexanes (22 mg, 47%).

Workup

  1. additionPS-dimethylaminoethyl resin was added
  2. waitthe stirring was continued for 2 h
  3. customthe resin removed by filtration
  4. customThe solvent was removed under a stream of N2
  5. customthe residue purified by preparative TLC
  6. washeluting with 25% ethyl acetate in hexanes (22 mg, 47%)

Sources & evidence

ORD record
ord-d837bc0afad24823b16c077db501a874
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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