Diisopropylethylamine → Rac-cis-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-cyclopentanecarboxylic acid methyl ester

HRID 737212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 737212
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[C:10]([OH:12])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:46][C:47]1[S:48][CH:49]=[C:50]([C:52]2[CH:63]=[CH:62][C:55]([C:56]([NH:58][CH:59]3[CH2:61][CH2:60]3)=[O:57])=[CH:54][CH:53]=2)[N:51]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[C:10](=[O:12])[NH:46][C:47]1[S:48][CH:49]=[C:50]([C:52]2[CH:53]=[CH:54][C:55]([C:56](=[O:57])[NH:58][CH:59]3[CH2:61][CH2:60]3)=[CH:62][CH:63]=2)[N:51]=1)=[O: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 11344263rac-(1R,2S)-2-(methoxycarbonyl)cyclopentane-1-carboxylic acidHCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

Produkt 1

HCID 87485281Rac-cis-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-cyclopentanecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Rac-cis-cyclopentane-1,2-dicarboxylic acid monomethyl ester (172 mg) was dissolved in DMF (5 mL) and treated with HATU (1.1 eq. 470 mg) and DIEA (3 eq, 500 μL) and stirred for 15 minutes. Then 4-(2-amino-thiazol-4-yl)-N-cyclopropyl-benzamide (1 eq, 260 mg) was added and the mixture stirred at ambient temperature overnight. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. MS: 414.5.

Aufarbeitung

  1. stirringthe mixture stirred at ambient temperature overnight
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customthe solvents removed
  5. dissolutionThe resulting mixture was redissolved in 5 ml of 90% DMF
  6. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  7. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-dedc7d3e95cd494fb8737c7fbcb673e4
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595398B2

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