Triethylamine → HCID 21963186, compound

HRID 2211865Notes

Reaction equation

HRID 2211865 reaction equation
Cl.[N:2]1([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[S:10][N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:17][O:18][C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH2:27][C:28](O)=[O:29])=[C:21]([N+:31]([O-:33])=[O:32])[CH:20]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>C(Cl)Cl>[S:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:8]([N:2]2[CH2:7][CH2:6][N:5]([C:28](=[O:29])[CH2:27][C:22]3[CH:23]=[C:24]([O:25][CH3:26])[C:19]([O:18][CH3:17])=[CH:20][C:21]=3[N+:31]([O-:33])=[O:32])[CH2:4][CH2:3]2)=[N:9]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 270941(4,5-Dimethoxy-2-nitro-phenyl)-acetic acidHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 21963186HCID 21963186, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-piperazin-1-yl-benzoisothiazole hydrochloride (5.29 g, 20.7 mmol) and 4,5-dimethoxy-2-nitrophenylacetic acid (5 g, 20.7 mmol) were combined in 200 mL methylene chloride with triethylamine (5.77 mL, 41.4 mmol). This solution stirred for 15 min before bis-(2-oxo-3-oxazolidinyl) phosphinic chloride (5.26 g, 20.7 mmol) was added. After stirring overnight at rt, the reaction was quenched with water and extracted into methylene chloride. The organic layer was washed with 0.5 N HCl, water, sodium bicarbonate then water before it was dried over Na2SO4 and concentrated. The residue was taken up in methylene chloride and washed with water. The organic layer was dried over sodium sulfate, and concentrated then purified by MPLC using a Biotage prepacked silica gel cartridge eluting with 3% methanol in methylene chloride to afford 6.5 g of a tan solid. Yield 71%; 100% purity at 214 nm; LCMS (APCI): 443 [M+H]+; mp 170° C.

Workup

  1. additionwas added
  2. customthe reaction was quenched with water
  3. extractionextracted into methylene chloride
  4. washThe organic layer was washed with 0.5 N HCl, water, sodium bicarbonate
  5. dry with materialwater before it was dried over Na2SO4
  6. concentrationconcentrated
  7. washwashed with water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated
  10. customthen purified by MPLC
  11. washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-1facc705eb7b4d08a61be48c31eacc8d
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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