Reaktionsgleichung
C(NCC1SC([B:10]([OH:12])[OH:11])=CC=1)C.C(S(N1CCC(C2C3C(=C(C(N)=O)C=C([C:33]4[S:34][C:35]([CH2:38][NH:39][CH2:40][CH:41]([CH3:44])[CH2:42][CH3:43])=[CH:36][CH:37]=4)C=3)NC=2)CC1)(=O)=O)C.C(C1SC(B(O)O)=CC=1)=O.[BH3-]C#N.[Na+].CC(CC)CN>CO>[CH3:44][CH:41]([CH2:42][CH3:43])[CH2:40][NH:39][CH2:38][C:35]1[S:34][C:33]([B:10]([OH:12])[OH:11])=[CH:37][CH:36]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The {5-[(ethylamino)methyl]-2-thienyl}boronic acid used to prepare 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide was prepared as follows: A solution of (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol) in MeOH (0.5 mL) and a solution of NaCNBH3 (40 mg, 0.64 mmol) in MeOH (0.5 mL) were added to (2-methylbutyl)amine (28 mg, 0.32 mmol) in a 2-dram vial. The vial was capped and the reaction was stirred at room temperature for 20 h. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH), eluting in sequence with MeOH (6 mL) and a 2 M solution of NH3/MeOH (9 mL). The NH3/MeOH fraction was concentrated under a stream of nitrogen to give 43 mg of crude (5-{[(2-methylbutyl)amino]methyl}-2-thienyl)boronic acid.
Aufarbeitung
- customwas prepared
- customThe vial was capped
- filtrationThe reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH)
- washeluting in sequence with MeOH (6 mL)
- concentrationThe NH3/MeOH fraction was concentrated under a stream of nitrogen
Quellen und Nachweise
- ORD-Eintrag
- ord-2eaa9e26af4947c9ba519117a1c067a2
- Quelldatensatz
- uspto-grants-2011_11
- Patentnummer
- US08063071B2
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