Dimethylformamide → HCID 86617551, compound

HRID 2234433Notes

Reaction equation

HRID 2234433 reaction equation
[Cl:1][C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:14])[C:7](=[O:13])[CH2:8][CH2:9][NH:10]2)=[CH:4][N:3]=1.[H-].[Na+].Cl[CH2:18][CH:19]1[C:23]([CH3:24])=[CH:22][O:21][N:20]1C.[CH3:26]N(C=O)C>>[Cl:1][C:2]1[N:12]=[C:11]2[C:5](=[CH:4][N:3]=1)[N:6]([CH3:14])[C:7](=[O:13])[CH2:8][CH2:9][N:10]2[CH2:24][C:23]1[C:19]([CH3:18])=[N:20][O:21][C:22]=1[CH3:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 18001973HCID 18001973, compoundHCID 866175762-Chloro-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one2×

Product 1

HCID 86617551HCID 86617551, compound

Procedure

To a stirred solution of 10-chloro-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 100; 64 mg, 0.3 mmol) in DMF (2 mL) was added sodium hydride (60% mineral oil dispersion; 18 mg, 0.36 mmol) and the solution stirred at room temperature until effervescence had ceased. 3 chloromethyl-2,4-dimethylisoxazole (Aldrich; 52 mg, 0.36 mmol) was added and the reaction heated at 50° C. with stirring overnight. The solvent was evaporated and residue dissolved in methanol, transferred to an SCX cartridge pre-wet with methanol, washed with methanol and eluted with methanolic ammonia. Product containing fractions were combined and evaporated to yield the title compound as an off white solid (82 mg, 85%)

Workup

  1. temperaturethe reaction heated at 50° C.
  2. stirringwith stirring overnight
  3. customThe solvent was evaporated
  4. dissolutionresidue dissolved in methanol
  5. washwashed with methanol
  6. washeluted with methanolic ammonia
  7. additionProduct containing fractions
  8. customevaporated

Sources & evidence

ORD record
ord-0322b398e26a410ca2b00981aa36d56c
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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