HCID 178507804, compound → HCID 135486169, compound

HRID 2211945Notes

Reaction equation

HRID 2211945 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]#[C:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[NH:16][N:15]=1>C(O)(=O)C>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([C:13]3[NH:1][C:2]4[C:3]([CH:12]=3)=[CH:4][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:6][CH:7]=4)=[N:15][NH:16]2)=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 178507804HCID 178507804, compound

Product 1

HCID 135486169HCID 135486169, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The alkyne (5-4, 56 mg, 0.161 mmol) was dissolved in acetic acid (8 mL) and treated with mercuric acetate (77 mg, 0.24 mmol). After 2 h stirring, the reaction mixture was concentrated in vacuo, suspended in saturated aqueous sodium bicarbonate and treated with sodium borohydride. After 10 min stirring, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 50% ethyl acetate in hexanes) afforded the desired product (5-5); 1H NMR (300 MHz, DMSO-d6) δ 13.58 (s, 1H), 12.09 (s, 1H), 8.26 (d, 1H, J=8.7 Hz), 8.11 (s, 1H), 7.72 (d, 1H, J=1.5 Hz), 7.61 (dd, 1H, J=8.7, 1.8 Hz), 7.55 (d, 1H, J=8.4 Hz), 7.36 (d, 1H, J=1.5 Hz), 7.30 (dd, 1H, J=8.7, 1.8 Hz), 7.16 (s, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiontreated with sodium borohydride
  3. stirringAfter 10 min stirring
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9057222ddc5445e7b44dc97c08932de9
Source dataset
uspto-grants-2006_09
Patent number
US07101884B2

Reaction notes

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