HCID 178522400, compound → HCID 178522403, compound

HRID 574674Notes

Reaction equation

HRID 574674 reaction equation
C([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([NH:17][C:18](=[O:32])[CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][N:11]=1)C1C=CC=CC=1>CO.[Pd]>[OH:16][C:14]1[C:13]([NH:17][C:18](=[O:32])[CH:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:12][N:11]=[C:10]([CH2:9][OH:8])[N:15]=1

Participants

4

Reactant 1

HCID 178522400HCID 178522400, compound

Product 1

HCID 178522403HCID 178522403, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of step D product, 3-f, (1.2 g, 2.8 mmol) in MeOH (100 mL) was added Pd/C (200 mg, 10%) and HCO2NH4 (0.36 g, 5.6 mmol). The mixture was stirred and refluxed for 5 h. The reaction mixture was filtered. The liquids were concentrated and purified by column chromatography to afford the product, 3-g (590 mg, 64%). 1H NMR (300 MHz, DMSO) δ 4.30 (d, J=4.2 Hz, 2H), 5.66 (s, 1H), 7.21-7.35 (m, 11H), 8.66 (s, 1H), 9.64 (s, 1H). LC-MS (M+H)+ 326.1.

Workup

  1. temperaturerefluxed for 5 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe liquids were concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-8256f2410a014018b82eadd32470eb63
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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