Diisopropylethylamine → {4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazin-1-yl}-acetic acid ethyl ester

HRID 253871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253871
[CH:1]1([N:7]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[NH:9][C:10]2[S:11][C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1([C:31](=[O:39])[CH2:32][N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)CCOCC1.CN(C([O:47]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:70]([CH3:72])C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH2:70]([O:47][C:31](=[O:39])[CH2:32][N:33]1[CH2:34][CH2:35][N:36]([C:15]([C:12]2[S:11][C:10]([NH:9][C:8]([N:7]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:18])=[N:14][CH:13]=2)=[O:17])[CH2:37][CH2:38]1)[CH3:72]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 1006221-(Morpholinocarbonylmethyl)piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114054472-(3,3-Dicyclohexylureido)thiazole-5-carboxylic acid

Produkt 1

HCID 57883964{4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazin-1-yl}-acetic acid ethyl esterAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), 1-morpholin-4-yl-2-piperazin-1-yl-ethanone (39 mg, 0.23 mmol), and HBTU (74 mg, 0.19 mmol) were weighed out and added to a 25 mL reaction flask. DMF (2 mL) and DIEA (52 μL, 0.30 mmol) were added. The reaction was stirred under nitrogen at ambient temperature overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aqueous NH4Cl (10 mL). After separation and extraction with EtOAc (2×5 mL) the combined organic portions were dried over MgSO4. Purification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2) afforded 37 mg (49%) of the desired compound.

Aufarbeitung

  1. additionadded to a 25 mL reaction flask
  2. customquenched with saturated aqueous NH4Cl (10 mL)
  3. customAfter separation and extraction with EtOAc (2×5 mL) the combined organic portions
  4. dry with materialwere dried over MgSO4
  5. customPurification with silica gel chromatography (10% EtOAc and 1% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-270b6784532149d5b8f37103b28cc805
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872139B2

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