HCID 18381662, compound → HCID 18381614, compound

HRID 2297448Notes

Reaction equation

HRID 2297448 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1>[Pd]>[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1

Participants

3

Reactant 1

HCID 18381662HCID 18381662, compound

Product 1

HCID 18381614HCID 18381614, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(5-phenyl-pent-1-ynyl)-phthalazine (770 mg, 1.665 mmoles), prepared as described in example 66, in THE (50 ml). was hydrogenated in Parr in the presence of 10% Pd/C (100 mg) for 24 hours. The catalyst was filtered off and the hydrogenation was kept on for further 24 hours at room temperature and for 5 hours at 80° C. The solution was brought to dryness and flash chromatographed (eluent: petrolatum/ethyl acetate 1:1). The fractions corresponding to the starting compound were brought to dryness and hydrogenated again for 24 hours, then worked up as above. The fractions containing the desired product were joined to the previously obtained ones, dissolved in ethyl acetate and acidified with HCl/ethyl acetate. The precipitate was filtered and crystallised from ethanol (2 ml) and ethyl acetate (8 ml) by subsequent concentration. There were yielded 142 mg of the title compound (yield: 17%). m.p.: 170-173° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customchromatographed (eluent: petrolatum/ethyl acetate 1:1)
  3. waitThe fractions corresponding to the starting compound were brought to dryness and hydrogenated again for 24 hours
  4. additionThe fractions containing the desired product
  5. dissolutiondissolved in ethyl acetate
  6. filtrationThe precipitate was filtered
  7. customcrystallised from ethanol (2 ml) and ethyl acetate (8 ml) by subsequent concentration

Sources & evidence

ORD record
ord-fea474cd02834736894a0d0b9a670d38
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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