Trifluoroacetic acid → HCID 89783608, compound

HRID 1055942Notes

Reaction equation

HRID 1055942 reaction equation
[CH2:1]([CH:8]1[CH2:13][N:12](C(OC(C)(C)C)=O)[C:11](=[O:21])[C:10]2[CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)[NH:24][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([CH:8]1[CH2:13][NH:12][C:11](=[O:21])[C:10]2[CH:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)[NH:24][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89783873HCID 89783873, compound

Product 1

HCID 89783608HCID 89783608, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of rac-tert-butyl 7-benzyl-4-oxo-2-(quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-5(4H)-carboxylate (200 mg, 0.441 mmol), DCM (10 mL), and TFA (2 mL) was stirred at RT for 2 h. The mixture was concentrated in vacuo, and the residue was suspended in 1N aq. HCl (10 mL) and washed with EtOAc (5 mL). The aq. layer was neutralized with sat. aq. NaHCO3 (5 mL) and extracted with EtOAc (2×10 mL). The combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by preparative TLC (80% EtOAc/petroleum ether) afforded rac-7-benzyl-2-(quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (30 mg, 0.085 mmol, 19% yield) as a pale green solid: 1H NMR (400 MHz, DMSO-d6) δ 12.29 (1H, br s), 8.92 (1H, dd, J=1.6 Hz & 2.8 Hz), 8.47 (1H, dd, J=1.6 Hz & 6.8 Hz), 8.21 (1H, d, J=7.2 Hz), 7.86 (1H, d, J=8 Hz), 7.67-7.62 (2H, m), 7.43-7.40 (4H, m), 7.33-7.30 (1H, m), 7.18 (1H, d, J=2 Hz), 7.06 (1H, br s), 3.48-3.40 (1H, m), 3.20-3.10 (2H, m), 2.92-2.86 (2H, m). m/z (ESI, +ve) 353.9 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with EtOAc (5 mL)
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by preparative TLC (80% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-37b9a8ce614d47309b607e5ccf05c97b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…