HCID 59457955, compound → HCID 59457944, compound

HRID 547568Notes

Reaction equation

HRID 547568 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=2)[CH:3]=1>CO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:4]2[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH2:8])[N:5]=2)=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 59457955HCID 59457955, compound

Product 1

HCID 59457944HCID 59457944, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 9 (634 mg, 246 mmol) was hydrogenated in MeOH (50 mL) with 10% Pd/C (100 mg) at 45 Hg mm. for 20 h. The reaction mixture was filtered and evaporated to dryness to give 10 (550 mg, 99%); mp (MeOH) 230-233° C.; 1H NMR [(CD3)2SO] δ 8.96 (s, 1 H, NH), 7.70 (d, J=8.7 Hz, 1 H, H-3′), 7.65 (d, J=2.5 Hz, 1 H, H-6′), 6.95 (dd, J=8.8, 2.9 Hz, H-4′), 6.30 (s, 1 H, H-5), 5.94 (s, 2 H, NH2), 4.84 (s, 2 H, NH2), 2.07 (s, 3H, CH3); HRMS (FAB+) calc. for C10H13N6 (M+1) m/z 217.1202, found 217.1202; Anal. calc. for C10H12N6; C, 55.5; H, 5.6; N, 38.9; found C, 55.3; H, 5.7; N, 38.6%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-60ce8a36c7a542328646697c2fdc1d9f
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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