Sodium Hydroxide → HCID 22598944, compound

HRID 1007674Notes

Reaction equation

HRID 1007674 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([O:22]CC)=[O:21])=[CH:17][CH:18]=2)[CH:13]=[N:12]1.[OH-].[Na+]>C(O)C.O>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[N:12]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22598938HCID 22598938, compound

Product 1

HCID 22598944HCID 22598944, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product of step A (510 mg, 1.16 mmol) was dissolved in ethanol (50 mL) and sodium hydroxide (6.5 mL of a 1N solution, 6.5 mmol) added. The solution was heated at reflux for 1.5 hours, diluted with water (45 mL), and the ethanol removed under vacuum. The solution was acidified to pH=3 with 1N HCl (˜7 mL) with stirring. The resulting solids were filtered, washed with water, and dried under vacuum to afford the product (308 mg, 89%). LRMS (ES): 298.1 ([M+H]+. HRMS: Calculated for C15H16N5O2: 298.1304; Found: 298.1320. 1HNMR (600.1343 MHz, CDCl3): 12.5 (b, H), 8.42 (s, 1H), 8.26 (d, 2H), 8.19 (s, 1H), 7.90 (d, 1H), 7.67, (d, 1H), 7.45 (m, 1H), 6.58 (s, 1H), 4.50 (t, 2H), 3.29 (m, 2H), 2.13 (t, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1.5 hours
  3. customthe ethanol removed under vacuum
  4. filtrationThe resulting solids were filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-218e7850988f4770904f56d8fc2a95d6
Source dataset
uspto-grants-2004_09
Patent number
US06794518B1

Reaction notes

Loading…