Trifluoroacetic acid → HCID 89783521, compound

HRID 1055857Notes

Reaction equation

HRID 1055857 reaction equation
[C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:20]3[NH:28][C:27]4[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=4[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[N:11]=1.C(O)(C(F)(F)F)=O>CN(C=O)C.CS(C)=O>[CH2:7]([NH:8][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:20]3[NH:28][C:27]4[CH2:26][CH2:25][NH:24][C:23](=[O:29])[C:22]=4[CH:21]=3)[CH:14]=[CH:15][CH:16]=2)[N:11]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7504BenzylamineHCID 897835482-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89783521HCID 89783521, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Phenylmethanamine (0.144 g, 1.343 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.100 g, 0.336 mmol) were combined in 1 mL DMF, sealed, and heated to 100° C. overnight. The mixture was treated with TFA (0.104 ml, 1.343 mmol) and was diluted with 1 mL DMSO, filtered and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 5-60% ACN/H2O with 0.1% TFA); product-containing fractions were treated with saturated aq. NaHCO3 and DCM. The organic layer was separated and the aq. layer was extracted 3×DCM. The combined organic layers were then dried over Na2SO4, filtered, and concentrated in vacuo to give 2-(2-(benzylamino)-quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.011 g, 0.030 mmol, 9% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (1H, br. s), 7.88-8.01 (3H, m), 7.50 (1H, dt, J=7.7, 0.7 Hz), 7.39-7.45 (2H, m), 7.34 (2H, t, J=7.5 Hz), 7.21-7.28 (1H, m), 7.18 (1H, t, J=7.6 Hz), 6.88-7.00 (3H, m), 4.71 (2H, d, J=5.9 Hz), 3.34-3.38 (2H, m), 2.56-2.65 (2H, m). m/z (ESI, +ve) 369.0 (M+H)+.

Workup

  1. customsealed
  2. filtrationfiltered
  3. custompurified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 5-60% ACN/H2O with 0.1% TFA)
  4. additionproduct-containing fractions were treated with saturated aq. NaHCO3 and DCM
  5. customThe organic layer was separated
  6. extractionthe aq. layer was extracted 3×DCM
  7. dry with materialThe combined organic layers were then dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a34851f0757d4d72af3a5a337d3f01fd
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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