HCID 86619751, compound → HCID 11555060, compound

HRID 499183Notes

Reaction equation

HRID 499183 reaction equation
O=[C:2]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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:31])[C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[C:27]([F:30])([F:29])[F:28])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)=[O:6]>S(=O)(=O)(O)O>[F:26][C:24]1[CH:23]=[CH:22][C:21]([C:27]([F:29])([F:28])[F:30])=[C:20]([C:19]([N:16]2[CH2:17][CH2:18][N:13]([C:10]3[N:9]=[N:8][C:7]([C:5]4[O:6][C:2]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)=[CH:3][N:4]=4)=[CH:12][CH:11]=3)[CH2:14][CH2:15]2)=[O:31])[CH:25]=1

Participants

3

Reactant 1

HCID 86619751HCID 86619751, compound

Product 1

HCID 11555060HCID 11555060, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A few drops of concentrated sulfuric acid was added to 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-oxo-2-phenylethyl) amide (0.100 g, 0.194 mmol). This mixture was stirred at ambient temperature over night. The reaction was quenched with ice water, followed by the addition of 2 mL of 5% ammonia solution. The resulting mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulphate, then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid in 82% yield (0.079 g). m.p. 122-125° C. 1H NMR (300 MHz, CDCl3) δ 8.04 (d, J=9.6 Hz, 1H), 7.80-7.71 (m, 3H), 7.49-7.37 (m, 3H), 7.36-7.29 (m, 1H), 7.28-7.19 (m, 1H), 7.1-7.04 (m, 1H), 7.01 (d, J=9.6 Hz, 1H), 4.08-3.96 (1H), 3.93-3.71 (m, 5H), 3.4-3.32 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 166.1 158.8, 158.4, 152.5, 142.3, 129.8, 129.6, 128.9, 128.8, 127.6, 126.8, 125.1, 124.6, 123.4, 122.9, 116.8, 116.6, 114.9, 114.7, 112.4, 46.4, 44.7, 44.4, 41.4. MS (ES+) m/z 498.1 (M+1).

Workup

  1. customThe reaction was quenched with ice water
  2. additionfollowed by the addition of 2 mL of 5% ammonia solution
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-18a307bb98c449daa90f6a7d70671746
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

Loading…