Ethylenediamine → HCID 78107704, compound

HRID 510195Notes

Reaction equation

HRID 510195 reaction equation
[Cl: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](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C(N)CN.[OH-].[Na+]>CO.C1COCC1>[Cl: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 3

HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 89495495HCID 89495495, compound

Product 1

HCID 78107704HCID 78107704, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[5-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]amino}-3-methyl-N-(2,2,2-trifluoroethyl)butanamide 1-1a (315 mg, 0.543 mmol) dissolved in a mixture of MeOH (3.0 ml) and THF (7 ml) was added ethylenediamine (0.183 ml, 2.72 mmol) followed by 1 M sodium hydroxide (1.086 ml, 1.086 mmol). The mixture was allowed to stir for ½ hr at room temperature. The reaction was quenched with 1N HCL (2.7 mL), concentrated to remove solvents and aqueous sodium bicarbonate (10 mL) added. The product was extracted into DCM, dried over sodium sulfate, concentrated and chromatographed on silica using 1-10% methanol/dichloromethane to give 135 mg desired product 1-1b as a foam. LRMS (ESI) m/z 426.1 [(M+H)+; calcd for C19H19ClF3N5O: 426.1].

Workup

  1. customThe reaction was quenched with 1N HCL (2.7 mL)
  2. concentrationconcentrated
  3. customto remove solvents and aqueous sodium bicarbonate (10 mL)
  4. additionadded
  5. extractionThe product was extracted into DCM
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on silica using 1-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-5493268f69324737b1b881242f1443e4
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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