Diisopropylethylamine → (S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 737177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 737177
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1[S:51][CH:52]=[C:53]([C:55]2[CH:66]=[CH:65][C:58]([C:59]([NH:61][CH:62]3[CH2:64][CH2:63]3)=[O:60])=[CH:57][CH:56]=2)[N:54]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13](=[O:15])[NH:49][C:50]1[S:51][CH:52]=[C:53]([C:55]2[CH:56]=[CH:57][C:58]([C:59](=[O:60])[NH:61][CH:62]3[CH2:64][CH2:63]3)=[CH:65][CH:66]=2)[N:54]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14775612(S)-3-Boc-thiazolidine-2-carboxylic acidHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

Produkt 1

HCID 57849787(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-Thiazolidine-2,3-dicarboxylic acid 3-tert-butyl ester (49.4 mg, 0.21 mmol) was dissolved in DMF (2 mL). DIEA (74 μL, 0.42 mmol) was added followed by HATU (80.7 mg, 0.21 mmol). The reaction was stirred at ambient temperature for 15 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide (54.6 mg, 0.21 mmol) was added. The reaction was stirred at ambient temperature overnight and then heated to 50° C. for 7 hours. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 30.5 mg. MS: 475.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.54-0.75 (m, 4H), 1.22-1.47 (m, 9H), 2.79-2.90 (m, 1H), 3.05-3.25 (m, 2H), 3.55-3.75 (m, 1H), 5.33-5.50 (m, 2H), 7.78-7.98 (m, 5H), 8.40-8.48 (d, 1H), 12.50-12.59 (s, 1H).

Aufarbeitung

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. temperatureheated to 50° C. for 7 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-177bd830eebe4d178d796954300526e4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595398B2

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