Methanol → HCID 57863446, compound

HRID 1446760Notes

Reaction equation

HRID 1446760 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[N:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][N:32]3[C:35]([C:38]4[CH:43]=[CH:42][C:41]([CH2:44][C:45]([NH:47][C:48]5[CH:53]=[CH:52][CH:51]=[C:50]([C:54]([F:57])([F:56])[F:55])[CH:49]=5)=O)=[CH:40][CH:39]=4)=[CH:36][N:37]=[C:31]3[CH:30]=2)=[CH:25][CH:24]=1.CO>CN(C)P(N(C)C)(N(C)C)=O>[N:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][N:32]3[C:35]([C:38]4[CH:43]=[CH:42][C:41]([CH2:44][C:45]([NH:47][C:48]5[CH:53]=[CH:52][CH:51]=[C:50]([C:54]([F:57])([F:56])[F:55])[CH:49]=5)=[S:10])=[CH:40][CH:39]=4)=[CH:36][N:37]=[C:31]3[CH:30]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 87949Lawesson's reagentHCID 11525707HCID 11525707, compound

Product 1

HCID 57863446HCID 57863446, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
80 °C

Procedure

Add Lawesson's reagent (0.246 g, 0.61 mmol, 1.2 eq.) to the solution of 2-[4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-acetamide (0.240 g, 0.51 mmol, 1.0 eq.) in hexamethylphosphoramide (2.5 mL). Stir the reaction mixture at 80° C. overnight. Cool the mixture down to room temperature and load onto a Varian MegaElut® SCX cartridge (5 gram cartridge prewashed with methanol). Rinse with methanol to remove impurities then elute crude product with 2 M NH3 in methanol. Concentrate this solution in vacuo then purify HPLC to give a yellow foam (0.078 g, 31%). MS (ES), m/z 489 (M+1).

Workup

  1. washRinse with methanol
  2. customto remove impurities
  3. washthen elute crude product with 2 M NH3 in methanol
  4. concentrationConcentrate this solution in vacuo

Sources & evidence

ORD record
ord-c92e339c6abd4f6ea6b870046d531fde
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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