1,2-Epoxy-3-methoxypropane → 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[1-(2-hydroxy-3-methoxy-propyl)-5-methyl-1H-pyrazol-3-yl]-benzamide

HRID 1988377Notes

Reaction equation

HRID 1988377 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[CH3:26][O:27][CH2:28][CH:29]1[CH2:31][O:30]1>CN(C)C=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[N:22]([CH2:31][CH:29]([OH:30])[CH2:28][O:27][CH3:26])[N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5]

Participants

4

Reactant 2

HCID 135891,2-Epoxy-3-methoxypropaneHCID 111875812-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide

Product 1

HCID 114537142-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-[1-(2-hydroxy-3-methoxy-propyl)-5-methyl-1H-pyrazol-3-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide (0.36 g, 1 mmol) and 2-methoxymethyl-oxirane (0.8 mL) was stirred in N,N-dimethylformamide (1.0 mL) at 90° C. for 12 h. The mixture was concentrated in vacuo. The residue was purified by reverse phase chromatography, followed by trituration (1:1:1 diethyl ether-dichloromethane-ethyl acetate) to afford the title compound (0.08 g). LCMS (m/z) 450.1 M+1

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-195f4c7506ad419ba5ecef17a38e0b41
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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