HCID 13098441, compound → HCID 14855138, compound

HRID 547517Notes

Reaction equation

HRID 547517 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[N:14]1[CH:13]=[CH:12][C:11]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[CH:5]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 13098441HCID 13098441, compound

Product 1

HCID 14855138HCID 14855138, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of compound A3 (7.26 g, 33.7 mmol) and 10% Pd/C in MeOH was hydrogenated for 2 h, filtered through a pad of Celite, and solvent evaporated. The residue was recrystallized from MeOH/H2O to give A4 as a pale yellow powder (5.43 g, 83%): mp. (MeOH/H2O) 170-171° C. 1H NMR [(CD3)2SO] δ8.48 (bs, 1 H, NH), 8.14-8.12 (m, 2 H, H-2′&6′), 6.96 (t, J=7.9 Hz, 1 H, H-5), 6.86-6.84 (m, 2 H, H-3′ & 6′), 6.43 (t, J=2.0 Hz, 1 H, H-2), 6.32 (dd, J=7.8, 1.3H, 1 H, H-6), 6.26 (dd, J=7.8, 1.5 Hz, 1 H, H-4) 5.07 (br s, 2 H, NH2); HRMS (EI+) calc. for C11H11N3 (M+) m/z 185.0953, found 185.0945; Anal. calc. for C11H11N3.0.125 H2O: C, 70.5; H, 6.1; N, 22.5; found, C, 70.6; H, 6.0; N, 22.7%.

Workup

  1. filtrationfiltered through a pad of Celite, and solvent
  2. customevaporated
  3. customThe residue was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-203b838f4f3f49c09813d2a4b20da1ae
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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