Triethylamine → N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenyl-propan-2-yl]-2-hydroxy-2-methyl-propanamide

HRID 13008

Reaction equation

HRID 13008 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]([O:17][C@@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:19]([NH2:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O:38][C:39]([CH3:44])([CH3:43])[C:40](Cl)=[O:41])(=O)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:19]([NH:21][C:40](=[O:41])[C:39]([OH:38])([CH3:44])[CH3:43])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 66812640(1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine

Product 1

HCID 25013488N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenyl-propan-2-yl]-2-hydroxy-2-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine (18 mg, 50 μmol) in dichloromethane (2 ml) was added triethylamine (100 μl), followed by 2-chloro-1,1-dimethyl-2-oxoethyl acetate (24 mg, 150 μmol). The stirring was continued for 20 min at r.t., then the solvent was removed under reduced pressure, and the residue dissolved in ethanol (1 ml). Aqueous sodium hydroxide solution (1 M, 1 ml) was added, and the mixture was stirrer at 80° C. for 30 min. Then it was cooled to r.t., acidified with TFA, and concentrated under reduced pressure. The product was purified by semi-prep. HPLC. Yield 22 mg (96%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethanol (1 ml)
  3. additionAqueous sodium hydroxide solution (1 M, 1 ml) was added
  4. customat 80° C.
  5. customfor 30 min
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by semi-prep

Sources & evidence

ORD record
ord-63416ee92917486c861a489544912710
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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