Acetic Acid → HCID 178520198, compound

HRID 2098178Notes

Reaction equation

HRID 2098178 reaction equation
C[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.O.[NH2:28]N.C(O)(=O)C>C(O)C>[NH: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 24654Hydrazine hydrate (1:1)HCID 68755357HCID 68755357, compound

Product 1

HCID 178520198HCID 178520198, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-N-(2-(3-(dimethylamino)acryloyl)thiophene-3-yl)-2-(naphthalen-1-yl)acetamide (185 mg, 0.51 mmol) in abs. ethanol (2 mL) was added hydrazine hydrate (0.2 ml, 4.11 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. The precipitate that formed was washed with methanol and collected filtration to afford N-(2-(1H-pyrazol-3-yl)thiophen-3-yl)-2-(naphthalen-1-yl)acetamide (50 mg, 30%). Method [7] m/z 334.0 (M+H); retention time=5.887. 1H-NMR (DMSO-d6) δ 12.92 (broad s, 1H), 10.37 (s, 1H), 8.09 (d, J=7.7 Hz, 1H), 7.92 (d, J=6.9 Hz, 2H), 7.86 (d, J=7.7 Hz, 1H), 7.77 (s, 1H), 7.66 (d, J=5.3 Hz, 1H), 7.61-7.47 (m, 4H), 7.36 (d, J=5.3 Hz, 1H), 6.36 (d, J=2.4 Hz, 1H), 4.19 (s, 2H).

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. customThe precipitate that formed
  7. washwas washed with methanol
  8. customcollected
  9. filtrationfiltration

Sources & evidence

ORD record
ord-aeb9dac034bf45dc88c6fa50f41bab92
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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