Triethylamine → HCID 86760291, compound

HRID 719382Notes

Reaction equation

HRID 719382 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([S:15](Cl)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.[NH2:22][C@@H:23]1[CH2:27][C:26](=[O:28])[N:25]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]1=[O:37].CCN(CC)CC.S(Cl)(Cl)(=O)=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:30]([O:29][N:25]1[C:26](=[O:28])[CH2:27][C@@H:23]([NH:22][S:15]([N:12]2[CH2:13][CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:19])[F:1])=[CH:4][CH:5]=3)[CH2:10][CH2:11]2)(=[O:17])=[O:16])[C:24]1=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 24648Sulfuryl chlorideHCID 21898165HCID 21898165, compoundHCID 69150934HCID 69150934, compound

Product 1

HCID 86760291HCID 86760291, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl chloride (164 mg; 0.50 mmol), (3R)-3-Amino-1-benzyloxy-pyrrolidine-2,5-dione hydrochloric acid (102 mg; 0.40 mmol), Et3N (180 ul; 1.30 mmol) and DMAP (25 mg; 0.20 mmol) was dissolved in DMF (1 ml). The mixture was heated in a microwave oven at 200 W for 10 seconds and allowed to cool to room temperature. Another portion of the sulfonyl chloride (164 mg; 0.50 mmol) and Et3N (180 ul; 1.30 mmol) in DMF (1 ml) was added followed by heating for 10 seconds at 200 W. Reaction mixture were evaporated and filtered through Si-60 gel with EtOAC:Heptane as eluent. This crude product was purified on a C-18 column with an HPLC system using a gradient: 70% (H2O+0.1% TFA):30% (MeCN+0.1% TFA) to 100% (MeCN+0.1% TFA), gradient time=35 min, flow=10 ml/min, UV=220 nm. Fractions containing the product was evaporated to a small volume, the water phase was neutralised with 5% NaHCO3 and the product was extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and evaporated to give the title compound as a colourless solid. Obtained 94 mg (45%)

Workup

  1. temperatureThe mixture was heated in a microwave oven at 200 W for 10 seconds
  2. temperatureby heating for 10 seconds at 200 W
  3. customReaction mixture
  4. customwere evaporated
  5. filtrationfiltered through Si-60 gel with EtOAC
  6. customThis crude product was purified on a C-18 column with an HPLC system
  7. customto 100% (MeCN+0.1% TFA), gradient time=35 min, flow=10 ml/min, UV=220 nm
  8. additionFractions containing the product
  9. customwas evaporated to a small volume
  10. extractionthe product was extracted with EtOAc
  11. dry with materialThe organic phase was dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-336122960e1e4effa795cbb3160181f6
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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