Trifluoromethanesulfonic anhydride → HCID 25234774, compound

HRID 1670587Notes

Reaction equation

HRID 1670587 reaction equation
[CH2:1]([N:4]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)[S:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:18][CH2:17][C@@H:16](O)[C:15]2=[O:20])=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[Cl:50][C:51]1[CH:52]=[C:53]2[C:58](=[CH:59][CH:60]=1)[NH:57][CH2:56][CH2:55][CH2:54]2>C(Cl)Cl>[CH2:1]([N:4]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)[S:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:18][CH2:17][C@H:16]([N:57]3[C:58]4[C:53](=[CH:52][C:51]([Cl:50])=[CH:60][CH:59]=4)[CH2:54][CH2:55][CH2:56]3)[C:15]2=[O:20])=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 111828396-Chloro-1,2,3,4-tetrahydroquinolineHCID 57665819HCID 57665819, compound

Product 1

HCID 25234774HCID 25234774, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

Prepared using General Procedure 4, Method A. To a stirring solution of (R)-N-allyl-6-(3-hydroxyl-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide (75 mg, 0.20 mmol) in DCM (0.6 mL), under N2, was added diisopropylethylamine (70 μL, 0.40 mmol). The solution was then cooled to −40° C. in a dry ice/acetone bath and triflic anhydride was added (37 μL, 0.22 mmol). The reaction was stirred at −40° C. for 30 minutes then a solution of 6-chloro-1,2,3,4-tetrahydroquinoline (50 mg, 0.30 mmol) dissolved in DCM (0.3 mL) was added. The solution was allowed to warm to −20° C. and was placed in the −20° C. freezer overnight. The solution was then allowed to warm to room temperature and was washed with saturated aqueous NaHCO3 (5 mL), and the aqueous layer extracted once with DCM (5 mL). The organic layers were combined and concentrated. The residue was purified by silica gel chromatography with 5%-70% EtOAc in hexanes to give (S)-N-allyl-6-(3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide (94 mg) in 89% yield. LC/MS (10%-99% CH3CN/H2O (0.05% TFA)), m/z: M+1 obs=530.1, tR=2.05 min.

Workup

  1. customPrepared
  2. additionwas added
  3. temperatureto warm to −20° C.
  4. customwas placed in the −20° C. freezer overnight
  5. temperatureto warm to room temperature
  6. washwas washed with saturated aqueous NaHCO3 (5 mL)
  7. extractionthe aqueous layer extracted once with DCM (5 mL)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography with 5%-70% EtOAc in hexanes

Sources & evidence

ORD record
ord-7d317dffb4474d2c97199fa20f901883
Source dataset
uspto-grants-2011_08
Patent number
US07994174B2

Reaction notes

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