Ethylenediamine → N2-[5-(5-amino-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][C@H:18]([C:22]([NH:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[O:23])[CH:19]([CH3:21])[CH3:20])[CH:14]=[N:15][CH:16]=3)=[CH:9][N:8](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.C(N)CN.[OH-].[Na+]>C(Cl)Cl.CS(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][C@H:18]([C:22]([NH:24][CH2:25][C:26]([F:27])([F:29])[F:28])=[O:23])[CH:19]([CH3:20])[CH3:21])[CH:14]=[N:15][CH:16]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution N2-{5-[5-(amino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide 5-1b (50 mg, 0.093 mmol) in DCM (2 mL) was added TFA (1.4 mL, 18.6 mmol) and the resultant mixture was stirred for 2 h. The mixture was concentrated in vacuo, resuspended in MeOH (1 mL) and to this was added ethylenediamine (13 μl, 0.186 mmol) and sodium hydroxide (10 M aq) (0.065 mL, 0.652 mmol). After 18 h, the reaction was transferred to vial with an additional 1 mL of dimethylsulfoxide and this solution was purified by mass triggered reverse phase HLPC. The fractions containing product 5-1 were basified with NaHCO3, dried over MgSO4, filtered and concentrated. MS APCI: [M+H]+ m/z=407.1.
Workup
- concentrationThe mixture was concentrated in vacuo
- customthis solution was purified by mass triggered reverse phase HLPC
- additionThe fractions containing product 5-1
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6dbd7bd0c1624a61bb83b20ed94b9381
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096598B2
Reaction notes
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