Trifluoroacetic acid → HCID 68284190, compound

HRID 1527248Notes

Reaction equation

HRID 1527248 reaction equation
C([O:5][C:6](=[O:20])[CH2:7][N:8]1[C:12]2=[CH:13][N:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17](=[O:19])[CH3:18])=[CH:9]1)(C)(C)C.[C:21]([OH:27])([C:23]([F:26])([F:25])[F:24])=[O:22]>C(Cl)Cl>[F:24][C:23]([F:26])([F:25])[C:21]([OH:27])=[O:22].[C:17]([C:10]1[C:11]2[C:12](=[CH:13][N:14]=[CH:15][CH:16]=2)[N:8]([CH2:7][C:6]([OH:20])=[O:5])[CH:9]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283119HCID 68283119, compound

Product 1

HCID 68284190HCID 68284190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-acetyl-pyrrolo[2,3-c]pyridin-1-yl)-acetic acid tert-butyl ester (230 mg, 0.8 mmol) and TFA (0.915 mL, 11.95 mmol) in CH2Cl2 (3.1 mL) was stirred at RT overnight. The reaction mixture was concentrated and the residue was dried under high vacuum. The resulting solid was taken-up in Et2O and filtered to give the desired compound (TFA salt) as beige powder which was used in the next step without purification. MS (UPLC/MS): 219.2 [M+H]+, 217.2 [M−H]−; 1H-NMR (400 MHz, DMSO): δ (ppm): 9.50 (s, 1H), 9.03 (s, 1H), 8.54 (d, 1H), 8.51 (d, 1H), 5.40 (s, 2H), 2.57 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was dried under high vacuum
  3. filtrationfiltered

Sources & evidence

ORD record
ord-68f7476800b945bd9d40142c5aeca0a9
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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