Trifluoroacetic acid → (3-Acetyl-6-amino-pyrrolo[2,3-b]pyridin-1-yl)-acetic acid trifluoroacetate

HRID 1527262Notes

Reaction equation

HRID 1527262 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][N:8]1[C:12]2=[N:13][C:14]([NH:17]CC3C=CC(OC)=CC=3)=[CH:15][CH:16]=[C:11]2[C:10]([C:27](=[O:29])[CH3:28])=[CH:9]1)(C)(C)C.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]>C(Cl)Cl>[F:34][C:33]([F:36])([F:35])[C:31]([OH:37])=[O:32].[C:27]([C:10]1[C:11]2[C:12](=[N:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[N:8]([CH2:7][C:6]([OH:30])=[O:5])[CH:9]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283638[3-Acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 68284487(3-Acetyl-6-amino-pyrrolo[2,3-b]pyridin-1-yl)-acetic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [3-acetyl-6-(4-methoxy-benzylamino)-pyrrolo[2,3-b]pyridin-1-yl]-acetic acid tert-butyl ester (51 mg, 0.125 mmol) and TFA (191 μL, 2.49 mmol) in CH2Cl2 (0.6 mL) was stirred at RT for 24 h. Volatils were removed under reduced pressure and the brown solid thus obtained was used without further purification in the next step. MS (UPLC/MS): 234.1 [M+H]+, 232.1 [M−H]−. 1H-NMR (400 MHz, DMSO): δ (ppm): 8.08 (d, 1H), 8.02 (s, 1H), 6.83 (m, 2H), 6.44 (d, 1H), 4.90 (s, 2H), 2.38 (s, 3H).

Workup

  1. customVolatils were removed under reduced pressure
  2. customthe brown solid thus obtained
  3. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-baaaacbfc81e4a5b9f82dcbcd39b6c9c
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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