HCID 54153966, compound → HCID 53687760, compound

HRID 2268874Notes

Reaction equation

HRID 2268874 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1>C1COCC1.[Pd]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[C:14]([CH:21]=[CH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[CH:12]=[N:11][N:10]=1

Participants

4

Reactant 1

HCID 54153966HCID 54153966, compound

Product 1

HCID 53687760HCID 53687760, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-phenylethynyl-phthalazine (0.47 g, 1.12 mmoles), prepared as described in example 62, in THF (50 ml) was hydrogenated in Parr in the presence of 10% Pd/C (0.1 g) for 2 hours, then filtered, brought to dryness and flash chromatographed (eluent: petrolatum/ethyl acetate 1:1). The fractions containing the product were concentrated and taken up in 20 ml of ethyl ether/petrolatum 1:1. The crystallised was filtered and dried under vacuum at 40° C. to give 0.37 g of the title compound (yield: 78%). m.p.: 180-182° C.

Workup

  1. filtrationfiltered
  2. customchromatographed (eluent: petrolatum/ethyl acetate 1:1)
  3. additionThe fractions containing the product
  4. concentrationwere concentrated
  5. filtrationThe crystallised was filtered
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-d3c937cf604b48a296b5b97c2d34a577
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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