Diisopropylethylamine → (1R,3R)-3-(5-Amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanol
Reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:20]([O-])=O)[C:18](Cl)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([OH:30])[CH2:25]1.C(N(CC)C(C)C)(C)C.[H][H]>CO.[Pd]>[NH2:20][C:17]1[C:18]([NH:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([OH:30])[CH2:25]2)=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A stirred suspension of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (24.5 g, 72.6 mmol) in methanol (120 ml) was treated with (1R,3R)-3-Amino-cyclohexanol* (8.9 g, 76.3 mmol) and N,N-diisopropylethylamine (13.3 mL, 76.3 mmol), and stirred at 65° C. for three hours. The mixture was then cooled and 10% palladium on carbon (7.6 g, 3.6 mmol) was added. The mixture was pressurized to 100 psi with hydrogen and stirred at 50° C. for 18 h. Filtration and concentration afforded the desired product which was carried on directly into the next step. LCMS (Method P, ESI): RT=2.17 min, m+H=387.1. *Prepared following the procedures described in: P. Bernardelli et al./Tetrahedron: Asymmetry 15 (2004) 1451-1455
Workup
- temperatureThe mixture was then cooled
- stirringstirred at 50° C. for 18 h
- filtrationFiltration and concentration
Sources & evidence
- ORD record
- ord-206ba46d7bf64e14ade5c7a88ac5cd2a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461328B2
Reaction notes
Loading…