Acetonitrile → HCID 86645976, compound

HRID 1094323Notes

Reaction equation

HRID 1094323 reaction equation
COP([CH2:7][C:8](=O)[CH3:9])(=O)OC.C([O-])([O-])=O.[K+].[K+].[C:17]1([CH3:29])[CH:22]=[CH:21]C(S(N=[N+]=[N-])(=O)=O)=[CH:19][CH:18]=1.CC(C(=O)[C@@H](C1C=CC(N[C:44]2[S:45][CH:46]=[C:47]([C:49]([F:52])([F:51])[F:50])[N:48]=2)=CC=1)C)C=O.[CH3:54][C:55]#N>CO>[CH3:9][C@@H:8]([C:7]1[CH:19]=[CH:18][C:17]([CH2:29][C:44]2[S:45][CH:46]=[C:47]([C:49]([F:50])([F:51])[F:52])[N:48]=2)=[CH:22][CH:21]=1)[C:54]#[CH:55]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 13661p-Toluenesulfonyl azideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 86645977HCID 86645977, compound

Product 1

HCID 86645976HCID 86645976, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl-2-oxopropylphosphonate (0.25 ml, 1.2 mmol) was added to a suspension of K2CO3 (0.41 g, 3.0 mmol) and p-toluenesulfonylazide (0.24 g, 1.2 mmol) in CH3CN (15 ml). After stirring for 2 h a solution of (4R)-2-methyl-3-oxo-4-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)pentanal (0.34 g, 1.0 mmol) in CH3OH (5 ml) was added and the resulting mixture was stirred for 8 h at room temperature. The solvents were removed in vacuo and the residue diluted with Et2O (10 ml), washed with water (2×10 ml) and brine (2×5 ml) and dried over anhydrous Na2SO4. After solvent evaporation the crude was pulped in n-pentane to give 2-{4-[(1R)-1-methylprop-2-yn-1-yl]benzyl}-4-(trifluoromethyl)-1,3-thiazole (0.22 g, 0.745 mmol) as a colourless oil (75%). 1H-NMR (CDCl3): δ 8.68 (bs, 1H, NH); 7.85 (d, 2H, J=7 Hz); 7.55 (d, 2H, J=7 Hz); 7.15 (s, 1H), 3.50 (q, 1H, J=7 Hz); 3.25 (s, 1H), 1.50 (d, 3H, J=7 Hz).

Workup

  1. additionwas added
  2. customThe solvents were removed in vacuo
  3. additionthe residue diluted with Et2O (10 ml)
  4. washwashed with water (2×10 ml) and brine (2×5 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter solvent evaporation the crude

Sources & evidence

ORD record
ord-e04d93aa283a4e9795185a30d2704350
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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