반응 #748229

반응 방정식

tert-butyl 5-(phthalazin-6-yl)thiazol-2-ylcarbamate

Cs2CO3

4-(trifluoromethyl)benzyl-1-(4-nitrophenylsulfonyl)aziridine

K2CO3

mercaptoethanol

→

title compound

수율 19.0%

N—((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propyl)-5-(phthalazin-6-yl)thiazol-2-amine

수율 19.0%

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 15 minutes
2. 2
   기타After removing the solvent under reduced pressure
3. 3
   기타chromatographed through a Redi-Sep pre-packed silica gel column (40 g)
4. 4
   세척eluting with a gradient of 5% to 95% MeOH in DCM
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in DCM
6. 6
   workup.ADDITIONtreated with TFA

실험 절차

A solution of tert-butyl 5-(phthalazin-6-yl)thiazol-2-ylcarbamate (0.320 g, 0.97 mmol) and Cs2CO3 (0.63 g, 1.9 mmol) in DMF was stirred at room temperature for 30 minutes. The resulting solution was treated dropwise with ((S)-2-(4-(trifluoromethyl)benzyl-1-(4-nitrophenylsulfonyl)aziridine in DMF, and was then stirred for 30 minutes. The reaction was treated in portions with K2CO3 (0.67 g, 4.9 mmol) and mercaptoethanol (0.23 g, 2.9 mmol) and stirred for 15 minutes. After removing the solvent under reduced pressure, the residue was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 95% MeOH in DCM. The resulting residue was dissolved in DCM and treated with TFA to provide the title compound (0.100 g, 19% yield). LCMS (M+H) 430.6 calc. for C21H18F3N5S 430.6; 1H NMR (400 MHz, CDCl3-d) δ ppm 9.48 (s, 1H), 9.44 (s, 1H), 8.01 (d, 1H), 7.92 (d, 1H), 7.75 (s, 1H), 7.62 (sd, 3H), 7.35 (d, 2H), 3.92 (dd, 2H), 3.55 (dd, 1H), 3.25 (tt, 1H) 2.98 (dd, 1H), 2.89 (t, 2H), 2.72 (b, 1H).

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