Triethylamine → HCID 46869634, compound

HRID 1912476Notes

Reaction equation

HRID 1912476 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[C:6]=2[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=1.[CH3:28][S:29]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)(=[O:31])=[O:30].C(N(CC)CC)C>C1COCC1.O>[OH:18][C:14]1[CH:13]=[C:12]([C:11]2[C:6]3[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=[C:2]([N:35]4[CH2:36][CH2:37][N:32]([S:29]([CH3:28])(=[O:31])=[O:30])[CH2:33][CH2:34]4)[C:7]=3[N:8]=[C:9]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 46869088HCID 46869088, compound

Product 1

HCID 46869634HCID 46869634, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 9 (130 mg; 0.34 mmol), 1-(methylsulfonyl)piperazine (276 mg; 1.68 mmol) and N,N-diethylethanamine (170 mg; 1.68 mmol) in THF (3 mL) and water (3 mL) was stirred at 115° C. for 48 hours then concentrated in vacuo. The residue was taken up in EA, washed with aq. citric acid, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA/EtOH/AcOH, 90/10/1) afforded the title compound as an orange solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed with aq. citric acid
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (EA/EtOH/AcOH, 90/10/1)

Sources & evidence

ORD record
ord-69260631eabc4af692e5e5b000a6084e
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

Loading…