Acetic Anhydride → HCID 66849903, compound

HRID 2354810Notes

Reaction equation

HRID 2354810 reaction equation
[OH:1][CH:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)=[O:6].[C:37](OC(=O)C)(=[O:39])[CH3:38]>C(Cl)(Cl)Cl.C(N(CC)CC)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:31]1([CH:2]([O:1][C:37](=[O:39])[CH3:38])[CH2:3][NH:4][C:5]([C:7]2[N:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:30])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:29])[F:27])[CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[O:6])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 2

HCID 7918Acetic AnhydrideHCID 66849472HCID 66849472, compound

Product 1

HCID 66849903HCID 66849903, compoundYield 91.5%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-hydroxy-2-phenylethyl)amide (50 mg, 0.1 mmol) in chloroform (2 mL), acetic anhydride (0.25 mL), triethylamine (0.25 mL) and 4-dimethylaminopyridine (18 mg) were added. After stirred at ambient temperature for 6 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×10 mL) and dried over Na2SO4. The crude product obtained after removal of the solvent was purified by column chromatography eluted sequentially with hexane:ethyl acetate=1:1 and 1:2 to give a white powder (49.6 mg, 91.5% yield). 1H NMR (500 MHz, CDCl3) δ 8.10, 8.04, 7.75, 7.65, 7.57, 7.40-7.28, 7.00, 5.92, 4.07, 3.98, 3.90, 3.82-3.68, 3.36, 2.10. MS (ES+) m/z 508 (M+1).

Workup

  1. washwashed with water (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. customThe crude product obtained
  4. customafter removal of the solvent
  5. customwas purified by column chromatography
  6. washeluted sequentially with hexane

Sources & evidence

ORD record
ord-3e398de8c48541289d6208217b78c223
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

Loading…