[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid → HCID 178472930, Verbindung

HRID 2043898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043898
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].[CH3:17][CH:18]([CH3:29])[CH2:19][CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH3:28])[CH2:24][CH2:23]1.C1(N(CCC2C=CC=CC=2)C(=O)NC2SC(SC[C:46](O)=[O:47])=CN=2)CCCCC1>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH:15][C:46]([N:21]([CH2:20][CH2:19][CH:18]([CH3:29])[CH3:17])[C@H:22]2[CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][CH2:27]2)=[O:47])=[N:12][CH:11]=1)(=[O:8])=[O:9])[CH3:2]

Komponenten

6

Edukt 3

HCID 11993791[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acidHCID 213556364-methyl-N-(3-methylbutyl)cyclohexan-1-amineHCID 86253773(2-Amino-thiazole-5-sulfonylamino)acetic acid ethyl ester

Produkt 1

HCID 178472930HCID 178472930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customprepared
  3. additionwas added
  4. customThe reaction mixture was quenched with water
  5. customThe organic phase was isolated
  6. extractionthe aqueous phase was extracted with CH2Cl2
  7. customthe combined organic phases were dried
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in MeCN
  10. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-db205c7391d74f7388d201a05f4721f7
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586614B2

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