Sodium Methoxide → HCID 46241008, compound

HRID 2096214Notes

Reaction equation

HRID 2096214 reaction equation
[OH:1][C:2]1([C:29]2[S:33][C:32](S(C)(=O)=O)=[N:31][CH:30]=2)[CH2:7][CH2:6][CH:5]([N:8]2[CH2:11][CH:10]([NH:12][C:13]([CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:14])[CH2:9]2)[CH2:4][CH2:3]1.[CH3:38][O-:39].[Na+]>CN(C=O)C>[OH:1][C:2]1([C:29]2[S:33][C:32]([O:39][CH3:38])=[N:31][CH:30]=2)[CH2:3][CH2:4][CH:5]([N:8]2[CH2:9][CH:10]([NH:12][C:13]([CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:14])[CH2:11]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 46240784HCID 46240784, compound

Product 1

HCID 46241008HCID 46241008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-({1-[4-Hydroxy-4-(2-methanesulfonyl-thiazol-5-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (less polar isomer, 47a, 100 mg, 0.18 mmol) was treated with NaOMe (Aldrich, 0.5 M in MeOH, 1 mL) in DMF (1 mL) at 80° C. for 4 hours. The crude solution was directly purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe crude solution was directly purified by a CombiFlash® system

Sources & evidence

ORD record
ord-62f58eab45d04789b36982a8488197f0
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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