5-(2-((Tetrahydro-2H-pyran-2-yl)oxy)propyl)isoxazole-3-carboxylic acid → N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)isoxazole-3-carboxamide

HRID 872887Notes

Reaction equation

HRID 872887 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH3:18])[CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]([OH:17])=O)[CH:11]=1.[NH2:19][C@@H:20]([CH3:36])[CH2:21][N:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([Cl:35])[CH:28]=2)=[N:23]1>>[Cl:35][C:29]1[CH:28]=[C:27]([C:24]2[CH:25]=[CH:26][N:22]([CH2:21][C@@H:20]([NH:19][C:15]([C:12]3[CH:11]=[C:10]([CH2:9][CH:8]([O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH3:18])[O:14][N:13]=3)=[O:17])[CH3:36])[N:23]=2)[CH:34]=[CH:33][C:30]=1[C:31]#[N:32]

Participants

3

Reactant 2

HCID 671691425-(2-((Tetrahydro-2H-pyran-2-yl)oxy)propyl)isoxazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656330N-((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)isoxazole-3-carboxamide

Procedure

The title compound was prepared using the method of Example 34(d) starting from 5-(2-(tetrahydro-2H-pyran-2-yloxy)propyl)isoxazole-3-carboxylic acid (0.392 g, 1.534 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.2 g, 0.767 mmol). The product was purified by reverse phase flash chromatography. LC-MS: [M+1]=498.97.

Workup

  1. customThe product was purified by reverse phase flash chromatography

Sources & evidence

ORD record
ord-323fad724645421b9c139ebf9a50cd11
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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