HCID 9805035, compound → HCID 69831289, compound

HRID 2268930Notes

Reaction equation

HRID 2268930 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]#[C:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[N:16][N:17]=[C:18]2[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Pd]>[CH2:1]([N:8]([CH2:10][CH:11]=[CH:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[N:16][N:17]=[C:18]2[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33])[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 9805035HCID 9805035, compound

Product 1

HCID 69831289HCID 69831289, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl-{3-[1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl]-prop-2-ynyl}-methyl-amine (0.17 g, 0.36 mmoles), prepared as described in example 74, in THF (5 ml) and 10% Pd/C (0.07 g) was charged in a Parr apparatus at 2.7 atmospheres for 1.5 hours. The mixture was filtered over celite and dried to give an oil which was flash chromatographed (eluent: CH2Cl2/CH3OH/NH3 98:2:0.2, then 98:2:0.5). The resultant oil was crystallised from isopropyl ether to give 0.105 g of the title compound (yield: 61%).

Workup

  1. filtrationThe mixture was filtered over celite
  2. customdried
  3. customto give an oil which
  4. customchromatographed (eluent
  5. customThe resultant oil was crystallised from isopropyl ether

Sources & evidence

ORD record
ord-713684c62c7a4005a6328e2564c5c0f5
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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