HCID 135939589, compound → HCID 135939592, compound

HRID 1927276Notes

Reaction equation

HRID 1927276 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:23]=[C:13]3[NH:14][C:15](=[O:22])[C:16]4[C:21]([N:12]3[N:11]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:23]=[C:13]3[NH:14][C:15](=[O:22])[C:16]4[C:21]([N:12]3[N:11]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 135939589HCID 135939589, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135939592HCID 135939592, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of EXAMPLE 8 (1.07 g, 3.5 mmol) and 10% palladium on carbon (0.2 g) in methanol (25 mL) was stirred overnight under 1 atmosphere of hydrogen and filtered. The filtrate was concentrated and the residue crystallized from methanol to provide the title compound (0.58 g, 60%). 1H NMR (DMSO-d6) δ 12.23 (s, 1H), 8.10-8.18 (m, 2H), 7.86-7.95 (m, 1H), 7.49 (t, J=7.0 Hz, 1H), 7.19 (s, 1H), 7.05-7.12 (m, 2H), 6.56-6.63 (m, 1H), 6.20 (s, 1H), 5.19 (s, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue crystallized from methanol

Sources & evidence

ORD record
ord-b19bd12274b441108e39f967c5b52f4a
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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