Nitrogen → HCID 9951791, compound

HRID 2268849Notes

Reaction equation

HRID 2268849 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12][NH:11][N:10]=1.N#N.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25].[O:36]([CH3:38])[Na]>C1COCC1.CO>[CH3:38][O:36][C:24]([N:11]1[N:10]=[C:9]([CH2:8][C:7]2[C:6]([Cl:21])=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH2:12]1)=[O:25]

Participants

7

Reactant 4

HCID 947NitrogenHCID 682631,1'-CarbonyldiimidazoleHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-HCID 178418582HCID 178418582, compound

Product 1

HCID 9951791HCID 9951791, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1,2-dihydro-phthalazine (1 g, 3.1 mmoles), prepared as described in example 22, in THF (35 ml), under stirring and dry N2 at room temperature, was added with 1,1′-carbonyldiimidazole (0.55 ml, 3.41 mmoles). The mixture was refluxed for 1 hour. Dry CH3OH (2 ml) was added and the heating went on for further 2.5 hours. The mixture was cooled, poured into water/ice and extracted with CH2Cl2. The organic phases were washed with KHSO4, then with 5% NaOH, at last with water, anhydrified and concentrated to give a solid which was put in CH3OH with a catalytic amount of NaOCH3. The solution was refluxed for 1.5 hours, cooled, CH3OH was evaporated, the residue was taken up in water and CH2Cl2. The organic phases were washed with NaOH and water, anhydrified and concentrated to give a solid, which was triturated in CH3OH. 0.6 g of the title compound were obtained (yield: 52%). m.p.: 184-186° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customwent on for further 2.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with CH2Cl2
  5. washThe organic phases were washed with KHSO4
  6. concentrationwith 5% NaOH, at last with water, anhydrified and concentrated
  7. customto give a solid which
  8. temperatureThe solution was refluxed for 1.5 hours
  9. temperaturecooled
  10. customCH3OH was evaporated
  11. washThe organic phases were washed with NaOH and water, anhydrified
  12. concentrationconcentrated
  13. customto give a solid, which
  14. customwas triturated in CH3OH

Sources & evidence

ORD record
ord-bd2da4d8aa1a49de84de5da469c6d551
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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