Triethylamine → HCID 131726046, compound

HRID 719380Notes

Reaction equation

HRID 719380 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>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

6

Reactant 3

HCID 8471TriethylamineHCID 21898165HCID 21898165, compoundHCID 69151166HCID 69151166, compound

Product 1

HCID 131726046HCID 131726046, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(4-Trifluoromethyl-phenyl)-piperazine-1-sulfonyl chloride (256 mg; 0.78 mmol), (3S)-3-Amino-1-benzyloxy-pyrrolidine-2,5-dione hydrochloric acid (112 mg; 0.44 mmol), Et3N (230 ul; 1.65 mmol) and DMAP (43 mg; 0.35 mmol) was dissolved in DMF (2 ml). The mixture was heated in a microwave oven at 200 W for 2×10 seconds, allowed to cool to room temperature and then heated for another 10 seconds at 200 W. Evaporation of solvent and the residue was partitioned between EtOAc and 5% KHSO4, separation. Organic phase were washed with H2O and brine, the combined waterphases was extracted twice with warm DCM. Organic phases were combined and evaporated directly onto Si-60 gel. Purified by flash chromatography on 20 g of Si-60 gel using a gradient solvent system of 100% iso-Hexane to 100% EtOAc. Fractions containing the product was evaporated to give the title compound as a slightly yellow solid. Obtained 78 mg (35% yield). Purity by H-nmr was 90%, considered pure enough to use in next step.

Workup

  1. temperatureThe mixture was heated in a microwave oven at 200 W for 2×10 seconds
  2. temperatureheated for another 10 seconds at 200 W
  3. customEvaporation of solvent
  4. customthe residue was partitioned between EtOAc and 5% KHSO4, separation
  5. washOrganic phase were washed with H2O and brine
  6. extractionthe combined waterphases was extracted twice with warm DCM
  7. customevaporated directly onto Si-60 gel
  8. customPurified by flash chromatography on 20 g of Si-60 gel
  9. additionFractions containing the product
  10. customwas evaporated

Sources & evidence

ORD record
ord-8a8c9b2ff3cc48ed8bdc57e7a7e0600f
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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