Diisopropylethylamine → (1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl ester

HRID 2377988Notes

Reaction equation

HRID 2377988 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:50][O:51][C:52](=[O:60])[CH2:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][NH:55]1>CN(C=O)C.O>[CH3:50][O:51][C:52](=[O:60])[CH2:53][CH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][N:55]1[C:14]([C:9]1[N:10]=[C:11]([CH3:13])[S:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5214606Methyl piperidin-2-ylacetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acid

Product 1

HCID 66968203(1-{1-[5-(4-Fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoyl}-piperidin-2-yl)-acetic acid methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirring solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (3.00 g, 12.5 mmol) in DMF (50 ml), under argon was treated sequentially with N,N-diisopropylethylamine (6.8 ml), HATU (4.77 g, 12.5 mmol) then after stirring for 0.25 h, piperidin-2-yl-acetic acid methyl ester (Beckett et al, J. Med. Chem., 563,1969) (1.83 g, 12.5 mmol) was added. The mixture was stirred for 16 h at room temperature and was then diluted with water. The product was extracted into diethyl ether. The organic phase was washed with water (3×) and brine, was dried (MgSO4) and the solvent removed in vacuo to afford the title compound as a yellow gum (4.00 g, 85%).

Workup

  1. stirringThe mixture was stirred for 16 h at room temperature
  2. extractionThe product was extracted into diethyl ether
  3. washThe organic phase was washed with water (3×) and brine
  4. dry with materialwas dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0d2e7a20089140deadfe2b97b091f44d
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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