Triethylamine → HCID 91514082, compound

HRID 404923Notes

Reaction equation

HRID 404923 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:27][OH:28]>C(O)C.O>[OH:28][N:27]=[C:17]([C:14]1[S:13][C:12]([O:11][C:8]2[CH:9]=[N:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[N:16][CH:15]=1)[NH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 69198619HCID 69198619, compound

Product 1

HCID 91514082HCID 91514082, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of Example 81A (343 mg, 1.3 mmol) and triethylamine (0.9 ml, 6.5 mmol) in ethanol/water (95:5, v/v, 10 mL) was added hydroxylamine hydrochloride (228 mg, 3.25 mmol). The reaction was heated at reflux for 15 minutes and concentrated on a rotary evaporator. The residual solids were dissolved in dichloromethane (50 mL), and washed with water (50 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 372 mg of the title compound (96%) as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.30 (d, J=6.25 Hz, 6H) 5.11-5.33 (m, 1H) 6.03 (s, 2H) 6.84 (d, J=9.19 Hz, 1H) 7.61 (s, 1H) 7.78 (dd, J=9.01, 3.13 Hz, 1H) 8.22 (d, J=2.94 Hz, 1H) 9.71 (s, 1H); MS (ESI) m/z 295.0 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 minutes
  3. concentrationconcentrated on a rotary evaporator
  4. dissolutionThe residual solids were dissolved in dichloromethane (50 mL)
  5. washwashed with water (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-238954e6295440d78337613b4655f253
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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