HCID 59458015, compound → HCID 59458012, compound

HRID 547570Notes

Reaction equation

HRID 547570 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:27])[N:3]=1>[Pd].CO.C1COCC1>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([NH:15][C:12]2[CH:13]=[N:14][C:9]([NH:8][C:6]3[CH:5]=[C:4]([CH3:27])[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:10][CH:11]=2)=[O:26])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 59458015HCID 59458015, compound

Product 1

HCID 59458012HCID 59458012, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of 11 (790 mg, 2.16 mmol) in 1:1 MeOH/THF (100 ml) was added 10% Pd/C (100 mg) and hydrogenated at 45 Hg mm. for 20 h. The reaction mixture was filtered and evaporated to dryness and recrystallized from DCM/Pert.ether to give 12 (695 mg, 96%); mp (DCM/pet.ether)>300° C.; 1H NMR [(CD3)2SO] δ 9.78 (s, 1 H, NH), 9.45 (s, 1 H, NH), 8.63 (dd, J=2.4, 0.3 Hz, 1 H, H-2′), 8.09 (d, J=9.0 Hz, 1 H, H-5′), 7.98 (dd, J=9.0, 2.6 Hz, 1 H, H-4′), 7.72 (d, J=8.7 Hz, 2 H, H-2,6), 6.61 (d, J=8.7 Hz, 2 H, H-3,5), 6.43 (s, 1 H, H-5″), 6.13 (s, 2 H, NH2), 5.73 (s, 2 H, NH2), 2.12 (s, 3 H, CH3); HRMS (FAB+) calc. for C17H18N7O (M+1) m/z 336.1573, found 336.1578; Anal. calc. for C17H17N7O-0.25H2O: C, 60.1; H, 5.2; N, 28.9; C, 60.2; N, 5.3; N, 29.0%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customrecrystallized from DCM/Pert

Sources & evidence

ORD record
ord-f551bfb9e71947efb500e993e1b2fef4
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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