Acetic Acid → HCID 46869147, compound

HRID 1519964Notes

Reaction equation

HRID 1519964 reaction equation
[CH3:1][N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13](=[O:25])[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=O.C[NH:28]N.C(O)(=O)C>C(O)C>[CH3:1][N:2]1[CH:3]=[CH:4][C:5]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[NH:12][C:13](=[O:25])[CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[N:28]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 68755357HCID 68755357, compound

Product 1

HCID 46869147HCID 46869147, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-N-(2-(3-(dimethylamino)acryloyl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (Example 7.3.1., 143 mg, 0.39 mmol) in abs. ethanol (2 mL) was added methyl hydrazine (0.2 mL, 3.80 mmol) and acetic acid (0.5 mL, 8.73 mmol). The reaction mixture was stirred at room temperature overnight under N2(g) inlet and then concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and H2O. The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica, 20:80 ethyl acetate/hexane) yielded N-(2-(1-methyl-1H-pyrazol-3-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (27 mgs, 20%). Method [7] m/z 348.0 (M+H); retention time=5.328. 1H-NMR (CDCl3) δ 7.96 (d, J=5.2 Hz, 2H), 7.94-7.91 (m, 1H), 7.86 (d, J=7.8 Hz, 1H), 7.56-7.53 (m, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.36 (d, J=9.1 Hz, 1H), 7.32 (d, J=5.2 Hz, 1H), 7.15 (s, 1H), 7.09 (d, J=1.9 Hz, 1H), 5.17 (d, J=1.9 Hz, 1H), 4.13 (s, 2H), 3.45 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate and H2O
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 20:80 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8adc3e9d743346e2a0be3ad43760a478
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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