Ethylenediamine → N2-(5-{5-[(methylsulfonyl)amino]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridin-3-yl)-N-(2,2,2-trifluoroethyl)valinamide

HRID 510211Notes

Reaction equation

HRID 510211 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:14]([C:15]3[CH:16]=[C:17]([NH:21][C@H:22]([C:26]([NH:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=[N:19][CH:20]=3)=[CH:13][N:12](COCC[Si](C)(C)C)[C:9]2=[N:10][CH:11]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.C(N)CN.[OH-].[Na+]>C(Cl)Cl.CS(C)=O>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:14]([C:15]3[CH:16]=[C:17]([NH:21][C@H:22]([C:26]([NH:28][CH2:29][C:30]([F:33])([F:32])[F:31])=[O:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=[N:19][CH:20]=3)=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131733261N2-[5-(5-[(methylsulfonyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide

Product 1

HCID 117628588N2-(5-{5-[(methylsulfonyl)amino]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridin-3-yl)-N-(2,2,2-trifluoroethyl)valinamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N2-[5-(5-[(methylsulfonyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide 5-3a (57 mg, 0.093 mmol) from step 1 in DCM (2 mL) was added TFA (0.714 mL, 9.27 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 (0.013 mL, 0.185 mmol) and sodium hydroxide (10 M aq) (0.065 mL, 0.649 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 5-3 were basified with NaHCO3, dried over MgSO4, filtered and concentrated.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthis solution was purified by mass triggered reverse phase HLPC
  3. additionThe fractions containing product 5-3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8213ef325dc742a481498f69a64a96b4
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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