Dimethylformamide → (1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-ylthio)-1-phenylpropan-2-amine

HRID 1098883Notes

Reaction equation

HRID 1098883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([S:17][C@H:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:19]([NH:21]S(CC[Si](C)(C)C)(=O)=O)[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CN(C=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([S:17][C@H:18]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C@@H:19]([NH2:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 59339832N-((1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-ylthio)-1-phenylpropan-2-yl)-2-(trimethylsilyl)ethanesulfonamide

Product 1

HCID 59339625(1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-ylthio)-1-phenylpropan-2-amineYield 84%

Conditions

Temperature
95 °C

Procedure

To N-((1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-ylthio)-1-phenylpropan-2-yl)-2-(trimethylsilyl)ethanesulfonamide (103a, 0.042 g, 0.08 mmol) in DMF (2 mL) cesium fluoride (8.60 μL, 0.23 mmol) was added and the mixture was stirred at 95° C. Stirring was continued at that temperature O/N. Cooled at rt the solvent was removed and the mixture was partitioned between EtOAc/water the organic phase was than purified with HPLC The relevant fractions were collected freeze dried to give 24 mg of product (84% yield) which was analysed by LC/MS.

Workup

  1. stirringStirring
  2. temperatureCooled at rt the solvent
  3. customwas removed
  4. customthe mixture was partitioned between EtOAc/water the organic phase
  5. customthan purified with HPLC The relevant fractions
  6. customwere collected freeze
  7. customdried

Sources & evidence

ORD record
ord-5cba701f3274422b84220e05787608c0
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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