HCID 135890141, compound → HCID 136197415, compound

HRID 539869Notes

Reaction equation

HRID 539869 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][CH2:23][CH3:24])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]([CH2:17][CH3:18])=[C:12]([CH2:19][CH3:20])[N:11]=2)[CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][CH2:23][CH3:24])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]([CH2:17][CH3:18])=[C:12]([CH2:19][CH3:20])[N:11]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 135890141HCID 135890141, compound

Product 1

HCID 136197415HCID 136197415, compoundYield 108.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound (16.5 g, 50 mmol) of example 41 was dissolved in methanol, added with 0.4 g 10% Pd/C, and hydrogenized at the normal temperature and pressure. When hydrogen was not absorbed by the reaction mixture any more, the reaction was quenched and Pd/C was filtered off. The filtrate was concentrated to a small volume, and fed with HCl gas to generate a white solid. The obtained solid was filtered and dried to give the hydrochlorate of the title compound (16.4 g. yield: 97%). 1H NMR 1H NMR (CDCl3) δ: 7.68 (1H, d), 7.43 (1H, dd), 7.24 (1H, d), 4.04 (2H, t), 2.57 (2H, q), 2.46 (2H, q), 1.75 (2H, m), 1.19 (3H, t), 1.04 (3H, t), 0.96 (3H, t).

Workup

  1. customWhen hydrogen was not absorbed by the reaction mixture any more, the reaction
  2. customwas quenched
  3. filtrationPd/C was filtered off
  4. concentrationThe filtrate was concentrated to a small volume
  5. filtrationThe obtained solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-66404ce6030f4a489bcc3f8e84b2cb49
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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