1,2,3,4-Tetrahydro-1-naphthalenol → 1,2,3,4-Tetrahydronaphthalen-1-yl 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

HRID 573250

Reaktionsgleichung

Reaktionsgleichung von HRID 573250
[CH:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][C:32]1[N:36]([CH2:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51](O)=[O:52])[N:50]=3)[CH2:42][CH2:41]2)=[O:39])[N:35]=[C:34]([C:54]([F:57])([F:56])[F:55])[CH:33]=1>O1CCCC1>[CH3:31][C:32]1[N:36]([CH2:37][C:38]([N:40]2[CH2:41][CH2:42][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51]([O:11][CH:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:4][CH2:3][CH2:2]4)=[O:52])[N:50]=3)[CH2:44][CH2:45]2)=[O:39])[N:35]=[C:34]([C:54]([F:57])([F:55])[F:56])[CH:33]=1

Komponenten

5

Edukt 3

HCID 107231,2,3,4-Tetrahydro-1-naphthalenolHCID 11776TriphenylphosphineHCID 666014572-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarboxylic acid

Produkt 1

HCID 444627691,2,3,4-Tetrahydronaphthalen-1-yl 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At room temperature, 1,2,3,4-tetrahydronaphthalen-1-ol (155 mg) and triphenylphosphine (758 mg) are added to a solution of 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid (III-4, 380 mg) in tetrahydrofuran (2.5 ml). The mixture is stirred at 0 C under argon for 5 minutes, and diethyldiazene 1,2-dicarboxylate (383 mg) is then added dropwise. The reaction mixture is slowly warmed to room temperature. After 2 hours, the solvent is removed under reduced pressure and the residue is purified chromatographically. This gives 1,2,3,4-tetrahydronaphthalen-1-yl 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (196 mg, 39%).

Aufarbeitung

  1. waitAfter 2 hours
  2. customthe solvent is removed under reduced pressure
  3. customthe residue is purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-f11035b402324518b92dffa295e6e131
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029549B2

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