Hydrochloric Acid → HCID 59457939, compound

HRID 547571Notes

Reaction equation

HRID 547571 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15]C(=O)C)=[N:13][CH:14]=2)[CH:5]=[C:4]([CH3:19])[N:3]=1.Cl.O>O1CCOCC1.CO>[NH2:15][C:12]1[N:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:19])[N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 67200681HCID 67200681, compound

Product 1

HCID 59457939HCID 59457939, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A suspension of 4 (1.53 g, 5.19 mmol), in 1,4-dioxane/MeOH (1:1, 100 mL) and 2 N HCl [10 mL, H2O mL+c.HCl 2 mL)] was refluxed 24 h. The solvents were evaporated to dryness and the residue was basified with aq NH3. The resulting solution was extracted with EtOAc (110×50 mL), dried (Na2SO4) and evaporation of the solvent gave 5 (1.11 g, 99%). A small sample was recrystallized from DCM/Pet.ether; mp (DCM/Pet.ether) 183-186° C.; 1H NMR [(CD3)2SO] δ 8.41 (s, 1 H, NH), 8.01 (d, J=2.5 Hz, 1 H, H-2′), 7.56 (dd, J=8.7, ′), 6.42 (d, 2.6 Hz, 1 H, H-4 J=8.8 Hz, 1 H, H-5′), 5.90 (s, 2 H, NH2), 5.67 (s, 1 H, H-5), 5.59 (s, 2 H, NH2H, CH), 2.03 (s, 33) HRMS (EI+) calc. for C10H12N6 (M+) m/z 216.1123, found 216.1124; Anal. Calc. for C10H12N6.0.25H2O: C, 54.4; H, 5.7; N, 38.1; found, C, 54.4; H, 5.7; N, 37.9%.

Workup

  1. customThe solvents were evaporated to dryness
  2. extractionThe resulting solution was extracted with EtOAc (110×50 mL)
  3. customdried
  4. custom(Na2SO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-0ce3569e13814c33931b002456cc8134
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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