Dimethylamine → HCID 46240892, compound

HRID 2096212Notes

Reaction equation

HRID 2096212 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][NH:39][CH3:40]>CN(C=O)C>[CH3:38][N:39]([CH3:40])[C:32]1[S:33][C:29]([C:2]2([OH:1])[CH2:3][CH2:4][CH:5]([N:8]3[CH2:9][CH:10]([NH:12][C:13]([CH2:15][NH:16][C:17](=[O:28])[C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=4)=[O:14])[CH2:11]3)[CH2:6][CH2:7]2)=[CH:30][N:31]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 46240784HCID 46240784, compound

Product 1

HCID 46240892HCID 46240892, 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) and dimethylamine (Aldrich, 40% in water, 2 mL) in DMF (1 mL) was heated to 120° C. in a sealed tube overnight. 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-488d7c8b32bb4517bace88244d82b4b1
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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