Nitrogen → HCID 9864542, compound

HRID 2268846Notes

Reaction equation

HRID 2268846 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(N(CC)CC)C.[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>C1COCC1>[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][N:11]([C:31](=[O:34])[CH2:32][CH3:33])[N:10]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 9797215Phthalazine, 4-[(3,5-dichloro-4-pyridinyl)methyl]-1,2-dihydro-7-methoxy-

Product 1

HCID 9864542HCID 9864542, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 dropwise added with triethylamine (1.08 ml, 7.76 mmoles), then, at 0° C., with propionyl chloride (0.323 ml, 3.72 mmoles). After 10 minutes the mixture was brought to room temperature and after 3 hours poured into water/ice and THF was evaporated. The mixture was extracted more times with CH2Cl2 and the organic phases were washed with 5% NaOH and water, anhydrified and brought to dryness to give a solid which was crystallised from acetonitrile (50 ml). 1 g of the title compound was obtained (yield: 86%). m.p.: 195-197° C.

Workup

  1. customat 0° C.
  2. customwas evaporated
  3. extractionThe mixture was extracted more times with CH2Cl2
  4. washthe organic phases were washed with 5% NaOH and water
  5. customto give a solid which
  6. customwas crystallised from acetonitrile (50 ml)

Sources & evidence

ORD record
ord-6e03a02111b04981beb8abde3534c1f1
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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