Triethylamine → HCID 21876582, compound

HRID 1991271Notes

Reaction equation

HRID 1991271 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([N:14]3C(C)=CC=C3C)=[CH:9][C:8]=2[F:21])[CH2:3][CH2:2]1.Cl.NO.C(N(CC)CC)C>C(O)C.C1COCC1>[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:8]([F:21])=[CH:9][C:10]([NH2:14])=[CH:11][C:12]=2[F:13])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21877772HCID 21877772, compound

Product 1

HCID 21876582HCID 21876582, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of 1-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2,5-dimethyl-1H-pyrrole (0.828 g, 2.71 mmol) in 95% ethanol/THF (10:1, 55 mL) is added hydroxylamine hydrochloride (3.77 g, 54.2 mmol) and triethylamine (3.8 mL, 27.1 mmol). The reaction mixture is heated at reflux for 2 days and then concentrated under reduced pressure, diluted with CH2Cl2 (60 mL), washed with water (3×20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge, eluting with 10-20% EtOAC/Hexanes, affords the title compound, MS (ESI+) for C11H11F2NS m/z 228 (M+H)+; 1H NMR (CDCl3, 400 MHz) δ 6.22 (m, 2 H), 5.91 (m, 1 H), 3.83 (m, 2 H), 3.33 (m, 2 H), 2.86 (t, 2 H), 2.53 (m, 2 H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 days
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with CH2Cl2 (60 mL)
  5. washwashed with water (3×20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge
  9. washeluting with 10-20% EtOAC/Hexanes

Sources & evidence

ORD record
ord-ad5dd23ac5d946278398f67d407b8425
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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