Ethylenediamine → N2-{5-[5-(acetylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[CH:15]=[C:16]([NH:20][C@H:21]([C:25]([NH:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[O:26])[CH:22]([CH3:24])[CH3:23])[CH:17]=[N:18][CH:19]=3)=[CH:12][N:11](COCC[Si](C)(C)C)[C:8]2=[N:9][CH:10]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C(N)CN.[OH-].[Na+]>C(Cl)Cl.CS(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:13]([C:14]3[CH:15]=[C:16]([NH:20][C@H:21]([C:25]([NH:27][CH2:28][C:29]([F:31])([F:32])[F:30])=[O:26])[CH:22]([CH3:24])[CH3:23])[CH:17]=[N:18][CH:19]=3)=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)(=[O:3])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the above residue from Step 1 in DCM (2 mL) was added TFA (2.0 mL, 26 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, 0.187 mmol) and sodium hydroxide (10 M aq) (0.065 mL, 0.653 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 5-2 were basified with NaHCO3, dried over MgSO4, filtered and concentrated.
Workup
- concentrationThe mixture was concentrated in vacuo
- customthis solution was purified by mass triggered reverse phase HLPC
- additionThe fractions containing product 5-2
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5ea4d66e5b87419cb246ea374fa93afd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096598B2
Reaction notes
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