N2-{5-[5-(benzylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide → 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

HRID 510206Notes

Reaction equation

HRID 510206 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]3[CH:19]=[C:20]([NH:24][C@H:25]([C:29]([NH:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[O:30])[CH:26]([CH3:28])[CH3:27])[CH:21]=[N:22][CH:23]=3)=[CH:16][N:15]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:12]2=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]3[CH:19]=[C:20]([NH:24][C@H:25]([C:29]([NH:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[O:30])[CH:26]([CH3:28])[CH3:27])[CH:21]=[N:22][CH:23]=3)=[CH:16][N:15]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 131733257N2-{5-[5-(benzylamino)-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 131733259N2-{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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N2-{5-[5-(benzylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide 5-1a (1.03 g, 1.643 mmol) in MeOH (4 mL) purged with nitrogen (3×) was added palladium hydroxide on carbon (0.540 mg, 0.769 μmol) added and mixture hydrogenated 1 atm for 22 h. The reaction was filtered over Celite and the residue was purified by preparative HPLC reverse phase (C-18), eluting with acetonitrile/water (0.1% TFA), to give product 5-1b. The combined product fractions were basified with NaHCO3, dried over MgSO4, filtered and concentrated. MS APCI: [M+H]+ m/z=537.0.

Workup

  1. additionadded
  2. filtrationThe reaction was filtered over Celite
  3. customthe residue was purified by preparative HPLC reverse phase (C-18)
  4. washeluting with acetonitrile/water (0.1% TFA)

Sources & evidence

ORD record
ord-ae17543efc62493f96944d6b286852f3
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

Loading…