Dimethylformamide → N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N-((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamide

HRID 661031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661031
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([NH:18][C:19](=[O:21])[CH3:20])[S:7][C:8]=1[C:9]1[S:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.[F:33][C:34]([F:58])([F:57])[C:35]1[CH:56]=[CH:55][C:38]([CH2:39][CH:40]2[CH2:42][N@@:41]2[S:43]([C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=2)(=[O:45])=[O:44])=[CH:37][CH:36]=1>C(Cl)Cl.CO>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([N:18]([CH2:42][C@@H:40]([NH:41][S:43]([C:46]2[CH:47]=[CH:48][C:49]([N+:52]([O-:54])=[O:53])=[CH:50][CH:51]=2)(=[O:44])=[O:45])[CH2:39][C:38]2[CH:55]=[CH:56][C:35]([C:34]([F:57])([F:33])[F:58])=[CH:36][CH:37]=2)[C:19](=[O:21])[CH3:20])[S:7][C:8]=1[C:9]1[S:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1

Komponenten

7

Edukt 4

HCID 6228Dimethylformamide2×HCID 10796Cesium carbonateHCID 57633920N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamideHCID 178526727HCID 178526727, Verbindung

Produkt 1

HCID 57931099N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N-((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamideAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a 50 mL round-bottomed flask was added N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamide (0.300 g, 0.936 mmol), Cs2CO3 (0.610 g, 1.87 mmol), and DMF (0.0721 mL, 0.936 mmol). The resulting solution was heated to 50° C. A DMF solution of (S)-2-(4-(trifluoromethyl)benzyl)-1-(4-nitrophenylsulfonyl)aziridine (0.724 g, 1.87 mmol) was added to the reaction dropwise, and the reaction mixture was monitored by LCMS. After approximately 30 minutes, the solvent was removed and the residue was taken up in EtOAc and washed with saturated sodium bicarbonate. The solution was dried over sodium sulfate, filtered and loaded onto a plug of silica gel. Chromatography through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 10% 2 M NH3.MeOH in DCM, to provide N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N—((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamide (0.290 g, 0.410 mmol, 43.8% yield). LCMS (M+H) 707 calc. for C29H26F3N6O6S3 707.1.

Aufarbeitung

  1. customthe solvent was removed
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. washChromatography through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 10% 2 M NH3

Quellen und Nachweise

ORD-Eintrag
ord-52363da1bcd34161a8639a5cfcccd14e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084479B2

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