HCID 18381662, compound → HCID 53755185, compound

HRID 2297447Notes

Reaction equation

HRID 2297447 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>C1COCC1.[Pd]>[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]([CH:21]=[CH: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

4

Reactant 1

HCID 18381662HCID 18381662, compound

Product 1

HCID 53755185HCID 53755185, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-5-(5-phenyl-pent-1-ynyl)-phthalazine (280 mg, 0.6 mmole), prepared as described in example 66, in THF (15 ml) was hydrogenated in Parr in the presence of 10% Pd/C (50 mg) for 1 hour, then filtered, brought to dryness and flash chromatographed (eluent: CH2Cl2/CH3OH 98:2). The separated oil was taken up in ethyl ether (5 ml) and crystallised. The yielded crystallised was filtered and dried under vacuum at 40° C. to give 120 mg of the title compound (yield: 43%). m.p.: 121-123° C.

Workup

  1. filtrationfiltered
  2. customchromatographed (eluent: CH2Cl2/CH3OH 98:2)
  3. customcrystallised
  4. customThe yielded crystallised
  5. filtrationwas filtered
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-64b6f31f26ea4292a3d9fa98d020c26c
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

Loading…