Nitrogen → HCID 18381598, compound

HRID 2297464Notes

Reaction equation

HRID 2297464 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[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)[C:12](=[O:21])[N:11]([CH2:22][C:23]([OH:25])=O)[N:10]=1.N#N.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:42][OH:43]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[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)[C:12](=[O:21])[N:11]([CH2:22][C:23]([NH:42][OH:43])=[O:25])[N:10]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 18381601HCID 18381601, compound

Product 1

HCID 18381598HCID 18381598, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-1-oxo-1H-phthalazin-2-yl]-acetic acid (0.61 g, 1.55 mmoles), prepared as described in example 90, in dry DMF (25 ml), pH under N2, was added with 1,1′-carbonyldiimidazole (0.38 g, 2.32 mmoles). The mixture was stirred at room temperature for 4 hours then cooled, added with hydroxylamine hydrochloride (0.18 g, 2.55 mmoles) and stirred overnight. A precipitate formed and the solution was dried under vacuum, then taken up in 10% NaOH. The stirring was kept on for 2 hours, then the solid was filtered, washed with water, then with acetone and ethyl ether. It was taken up in 5% HCl and stirred for 1 hour, then filtered and washed with water, acetone and ethyl ether. The solid was dried under vacuum at 50° C., crystallised from acetic acid (60 ml) and dried under vacuum at 40° C. to give 0.3 g of the title compound (yield: 40%).

Workup

  1. temperaturethen cooled
  2. stirringstirred overnight
  3. customA precipitate formed
  4. customthe solution was dried under vacuum
  5. customwas kept on for 2 hours
  6. filtrationthe solid was filtered
  7. washwashed with water
  8. stirringstirred for 1 hour
  9. filtrationfiltered
  10. washwashed with water, acetone and ethyl ether
  11. customThe solid was dried under vacuum at 50° C.
  12. customcrystallised from acetic acid (60 ml)
  13. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-fc0b4a22c3da440380d2326df06a5439
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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