Hydrochloric Acid → HCID 57754519, compound

HRID 227126Notes

Reaction equation

HRID 227126 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20](=[O:33])[C:21]3[CH:26]=[CH:25][C:24]([CH:27]4OCCC[O:28]4)=[CH:23][CH:22]=3)=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20]([C:21]3[CH:22]=[CH:23][C:24]([CH:27]=[O:28])=[CH:25][CH:26]=3)=[O:33])=[CH:10]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57754708HCID 57754708, compound

Product 1

HCID 57754519HCID 57754519, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carbonyl]-benzaldehyde was synthesized analogous to example 10 with 90 mg (0.18 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-[1,3]dioxan-2-yl-benzoyl)-1H-quinolin-4-one, 4 mL of 4 N HCl in dioxane. The crude product obtained was used directly for next step with 84 mg (0.4 mmol) of sodium triacetoxyborohydride, 0.2 mL (2.0 M, 0.4 mmol) of methylamine in THF, 2 mL of DCM. The crude product was purified by flash chromatograph to yield 35 mg of colorless solid. LC-MSD, m/z for C24H20N3O2Br [M+H]+: 462.3, [M+2H]+: 463.3. Reverse phase HPLC gradient acetonitrile 0.1% TFA 20-95% in 4 min: 0.581 min.

Workup

  1. customThe crude product obtained

Sources & evidence

ORD record
ord-40235d179c81432293c5c63e1a7b2505
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…