Diisopropylethylamine → (S)-N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amine

HRID 1922244

Reaktionsgleichung

Reaktionsgleichung von HRID 1922244
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:29]=[CH:28][C:17]4[N:18]=[C:19]([NH:21][C@H:22]5[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]5)[S:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[CH:39]1([S:42](Cl)(=[O:44])=[O:43])[CH2:41][CH2:40]1>CN1C(=O)CCC1>[CH:39]1([S:42]([N:24]2[CH2:25][CH2:26][CH2:27][C@H:22]([NH:21][C:19]3[S:20][C:16]4[CH:15]=[C:14]([O:13][C:11]5[CH:10]=[CH:9][N:8]=[C:7]([C:5]6[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=6)[CH:12]=5)[CH:29]=[CH:28][C:17]=4[N:18]=3)[CH2:23]2)(=[O:44])=[O:43])[CH2:41][CH2:40]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 57725571(S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine

Produkt 1

HCID 57725553(S)-N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amineAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To the solution of (S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine (7.6 mg, 18 μmol) and DIPEA (35 μL, 200 μmol) in 400 μL of NMP was added cyclopropanesulfonyl chloride (10 mg, 98 μmol). The reaction solution was stirred at 55 for 16 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give (S)—N-(1-(cyclopropylsulfonyl)piperidin-3-yl)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-amine (6.2 mg, 12 μmol) as white powder. ES/MS m/z 511.2 (MH+).

Aufarbeitung

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-effa16ef3c0146bb93bb2566e139016d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173689B2

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