Ethylenediamine → HCID 71548832, compound

HRID 510196Notes

Reaction equation

HRID 510196 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][CH:18]([CH:27]([CH3:29])[CH3:28])[C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O: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>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][CH:18]([CH:27]([CH3:29])[CH3:28])[C:19]([NH:21][CH2:22][C:23]([F:24])([F:25])[F:26])=[O:20])[CH:14]=[N:15][CH:16]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 1317332552-(5-(5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

Product 1

HCID 71548832HCID 71548832, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(5-(5-fluoro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-ylamino)-3-methyl-N-(2,2,2-trifluoroethyl)butanamide 1-2a (78 mg, 0.145 mmol) was dissolved in DCM (2 ml). TFA (1.114 ml, 14.45 mmol) was added and mixture allowed to stir for 1 hr. Reaction concentrated then resuspended in MeOH (4 ml) and ethylenediamine (0.020 ml, 0.289 mmol) and sodium hydroxide (10 M aqueous) (0.101 ml, 1.012 mmol) added. After 30 min the reaction was treated with HCL (1.012 ml, 1.012 mmol) concentrated in vacuo and the residue was purified by preparative HPLC Reverse phase (C-18). (5-95% Acetonitrile/0.1% TFA/water). Product fractions were treated with aq. NaHCO3, concentrated and product extracted into DCM and ethyl acetate. Extracts dried over sodium sulfate, filtered and concentrated to give white solid 1-2. (40 mg).

Workup

  1. customReaction
  2. concentrationconcentrated
  3. additionAfter 30 min the reaction was treated with HCL (1.012 ml, 1.012 mmol)
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by preparative HPLC Reverse phase (C-18)
  6. additionProduct fractions were treated with aq. NaHCO3
  7. concentrationconcentrated
  8. extractionproduct extracted into DCM and ethyl acetate
  9. dry with materialExtracts dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d1ce76072b7943bd8fbdc7f011c79067
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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