Triethylamine → N-[(1R,2S)-1-[1-(4-Fluorophenyl)-6-methyl-indazol-5-yl]oxy-1-phenyl-propan-2-yl]-2-hydroxy-acetamide

HRID 1098834Notes

Reaction equation

HRID 1098834 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:26][C@H:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@@H:28]([NH2:30])[CH3:29])=[C:22]([CH3:25])[CH:23]=3)[CH:18]=[N:17]2)=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[F:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:26][C@H:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C@@H:28]([NH:30][C:5](=[O:4])[CH2:6][OH:7])[CH3:29])=[C:22]([CH3:25])[CH:23]=3)[CH:18]=[N:17]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 59339631(1R,2S)-1-[1-(4-fluorophenyl)-6-methyl-indazol-5-yl]oxy-1-phenyl-propan-2-amine

Product 1

HCID 25012518N-[(1R,2S)-1-[1-(4-Fluorophenyl)-6-methyl-indazol-5-yl]oxy-1-phenyl-propan-2-yl]-2-hydroxy-acetamideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetoxyacetyl chloride (0.071 mL, 0.66 mmol) was added to a solution of (1R,2S)-1-(1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yloxy)-1-phenylpropan-2-amine (62 mg, 0.17 mmol) and triethylamine (0.18 mL, 1.3 mmol) in THF (2.5 mL) at r.t. The mixture was stirred overnight and concentrated. The residue was dissolved in methanol (2 mL) and 28% ammonia (2 mL) and stirred at r.t. overnight. The title compound (57 mg, 80%) was obtained after purification by semi-preparative HPLC.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (2 mL)
  3. stirring28% ammonia (2 mL) and stirred at r.t. overnight

Sources & evidence

ORD record
ord-4838c00e74294b319473d6c06c47b98f
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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