HCID 58168154, compound → HCID 58168331, compound

HRID 1029287Notes

Reaction equation

HRID 1029287 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[CH2:6][NH:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12](=[O:20])[NH:13][C:14]3[C:19]([C:10]=2[CH:9]=1)=[CH:18][CH:17]=[CH:16][N:15]=3)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[CH2:6][NH:7][C:8]1[CH:22]=[CH:21][C:11]2[C:12](=[O:20])[NH:13][C:14]3[C:19]([C:10]=2[CH:9]=1)=[CH:18][CH:17]=[CH:16][N:15]=3

Participants

4

Reactant 1

HCID 58168154HCID 58168154, compound

Product 1

HCID 58168331HCID 58168331, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

466 (21 mg, 0.6 mmol) was dissolved in MeOH (130 mL) then reduced by flow chemistry on an H-Cube instrument (Pd/C cartridge, flow rate of 1.9 mL/min, 10 bar). The reaction solution was concentrated and purified via prep-LC-MS to provide 467 (5 mg, 24% yield) as a white powder. LC-MS (M+H=317, obsd.=317). 1H NMR (400 MHz, DMSO-D6) δ 8.53 (d, J=9.0, 2H), 8.22 (s, 1H), 8.07 (d, J=8.6, 1H), 7.42 (s, 1H), 7.34 (d, J=5.0, 1H), 6.84 (m, 2H), 6.66 (dd, J=7.5, 20.2, 2H), 6.34 (s, 1H), 6.20 (s, 2H), 5.46 (s, 2H), 5.32 (s, 1H).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified via prep-LC-MS

Sources & evidence

ORD record
ord-125c170d2cf242909b0ca2fab2121334
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…