Acetoxyacetyl chloride → N-[(1R,2S)-1-(4-ethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

HRID 13012Notes

Reaction equation

HRID 13012 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:18]=[CH:17]3)[C@@H:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1)[CH3:2].C([O:33][CH2:34][C:35](Cl)=[O:36])(=O)C>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[N:18]=[CH:17]3)[C@@H:10]([NH:12][C:34](=[O:33])[CH2:35][OH:36])[CH3:11])=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 59339861(1R,2S)-1-(4-ethylphenyl)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}propan-2-amine

Product 1

HCID 25013489N-[(1R,2S)-1-(4-ethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

Procedure

Prepared as described in Example 5 using (1R,2S)-1-(4-ethylphenyl)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}propan-2-amine (20 mg, 50 μmol) and 2-chloro-2-oxoethyl acetate (21 mg, 150 μmol). Yield 21 mg (91%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5e98bf862be34d01a205adc1d9a42197
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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