Trifluoroacetic acid → Diethyl 1-(3-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521714Notes

Reaction equation

HRID 1521714 reaction equation
C(OC([NH:8][CH:9]([CH3:31])[CH:10]([N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:9]([CH3:31])[CH:10]([N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67236832Diethyl 1-{3-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 67236563Diethyl 1-(3-aminobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-{3-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (6.00 g, 13.8 mmol) in CH2Cl2 (20 mL) is added TFA (10 mL). The mixture is stirred at room temperature for 16 h. The mixture is concentrated under reduced pressure and the residue is partitioned between ethyl acetate and saturated NaHCO3 solution. The resulting white solid was collected by filtration and dried in vacuo to afford the title compound (3.83 g, 83%). LCMS: 334.80 (M+H+).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is partitioned between ethyl acetate and saturated NaHCO3 solution
  3. filtrationThe resulting white solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a75df8afce314d8c862e398c81a9dd9c
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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