Sodium Hydroxide → HCID 15666911, compound

HRID 1461790Notes

Reaction equation

HRID 1461790 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:27])[C:5]2[C:11]([CH3:12])=[C:10]([CH2:13][CH:14]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[CH2:15][CH3:16])[CH:9]=[N:8][C:6]=2[N:7]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[NH2:1][C:2]1[N:3]=[C:4]([NH2:27])[C:5]2[C:11]([CH3:12])=[C:10]([CH2:13][CH:14]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH2:15][CH3:16])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 15666910HCID 15666910, compound

Product 1

HCID 15666911HCID 15666911, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 4 (190 mg, 0.521 mmol) in Me2SO (17 mL) was treated with 1 N NaOH (0.75 mL). After 20 hours at 20°-23° C., the solution was found by TLC (CHCl3 -MeOH, 4:1) examination to contain a small amount of unchanged 4. More 1N NaOH (0.50 mL) was added to the solution, kept at 20°-23° C., and 2 hours later TLC showed completed disappearance of 4. The Me2SO was then removed by distillation in vacuo (less than 1 mm, bath to 45° C). The residue was dissolved in H2O (3 mL), and the resulting clear solution was carefully treated dropwise with 1N HCl to produce pH 5 and cause precipitation of 5 as a pale-beige solid. The mixture was chilled in a refrigerator for several hours before the solid was collected and dried; yield 165 mg (82%). Anal. Calcd. for C19H21N5O2.2H2O: C, 58.90; H, 6.50; N, 18.08. Found: C, 59.40; H, 6.14; N, 17.63. Spectral data: mass, m/z 352, MH+ for C19H21N5O2 ; UV λmax 234 nm (ε 39 300), 322 (7730) at pH 1; 235 nm (ε 37 800), 335 (6050) at pH 7; 236 nm (ε 37 600), 346 (6730) at pH 13.

Workup

  1. customkept at 20°-23° C.
  2. custom2 hours
  3. customThe Me2SO was then removed by distillation in vacuo (less than 1 mm, bath to 45° C)
  4. dissolutionThe residue was dissolved in H2O (3 mL)
  5. additionthe resulting clear solution was carefully treated dropwise with 1N HCl
  6. customto produce pH 5
  7. customprecipitation of 5 as a pale-beige solid
  8. temperatureThe mixture was chilled in a refrigerator for several hours before the solid
  9. customwas collected
  10. customdried

Sources & evidence

ORD record
ord-d0a2a6042e3c4bb38b97e53865add6fe
Source dataset
uspto-grants-1991_12
Patent number
US05077404

Reaction notes

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