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

HRID 13070Notes

Reaction equation

HRID 13070 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-295998ee926d4df18e5c6991e73b2853
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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