HCID 178418361, compound → HCID 178516889, compound

HRID 539545Notes

Reaction equation

HRID 539545 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]3[N:17]=[N:18][NH:19][CH:20]=3)=[C:9]([O:21]CC3C=CC=CC=3)[C:8]2=[O:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(Cl)Cl.CCOC(C)=O.CO.[Pd]>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][C:16]3[N:17]=[N:18][NH:19][CH:20]=3)=[C:9]([OH:21])[C:8]2=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178516875HCID 178516875, compound

Product 1

HCID 178516889HCID 178516889, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901258Dichloromethane ethyl acetate methanolSolvent

Procedure

To a solution of 158b (0.29 g, 1.01 mmol) in CH2Cl2:EtOAc:MeOH (2:2:1, 10 mL) was added 10% Pd on carbon (15 mg). Reaction was stirred under balloon hydrogen pressure for 5 h. Reaction mixture was filtered and solvent was evaporated. Column chromatography using gradient CH2Cl2:Acetone (max 20%) gave pure 159b (0.19 g, 64%) as a slightly brownish solid. 1H NMR (400 MHz, DMSO) δ 9.03 (s, 1H), 8.62 (s, 1H), 7.82 (d, J=7.6 Hz, 2H), 7.38 (m, 3H), 7.15 (d, J=6.6 Hz, 1H), 6.68 (d, J=6.4 Hz, 1H), 6.11 (t, J=6.7 Hz, 1H), 4.43 (t, J=6.4 Hz, 2H), 3.99 (m, 2H), 2.27 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 147.49, 129.71, 128.52, 127.99, 125.29, 120.42, 107.98, 66.61, 47.10, 29.27. (expected aromatic carbons=11; quaternary carbons can't be seen even after repeated cycles) HRMS (EI) calcd for C16H16N4O2 [M]+ 296.1273. found 296.1274.

Workup

  1. customReaction
  2. customReaction mixture
  3. filtrationwas filtered
  4. customsolvent was evaporated

Sources & evidence

ORD record
ord-f3f30145bd394aa9ba3ba732494672cc
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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