Dabco → HCID 24813637, compound

HRID 1711985Notes

Reaction equation

HRID 1711985 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22](OS(C(F)(F)F)(=O)=O)=[C:23]2[C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([NH:36][C@@H:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH3:38])=[N:28][N:27]=2)=[CH:18][CH:17]=1.N12CCN(CC1)CC2>CN(C)C=O>[C:8]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:22]2[CH:21]=[CH:20][C:19]3[C:24](=[CH:25][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[C:23]=2[C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([NH:36][C@@H:37]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH3:38])=[N:28][N:27]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 70017DiphenylphosphineHCID 86602158HCID 86602158, compound

Product 1

HCID 24813637HCID 24813637, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of NiCl2(dppe) (0.22 g, 0.42 mmol) in N,N-dimethylformamide (10 ml) was treated with diphenylphosphine (1.5 ml, 8.4 mmol) at 23° C. The resulting dark red solution was stirred at 120° C. for 30 min. Then a solution of trifluoromethanesulfonic acid 7-methoxy-1-[4-((R)-1-phenyl-ethylamino)-phthalazin-1-yl]-naphthalen-2-yl ester (2.3 g, 4.2 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 1.9 g, 17 mmol) in N,N-dimethylformamide (13 ml) was added via a syringe, the flask was washed with N,N-dimethylformamide (2 ml). The resulting green solution was stirred at 120° C. for 17 hrs. The mixture was concentrated under reduced pressure (20 mbar, 70° C. bath temperature). The residue was purified by flash chromatography on silica gel (toluene→toluene/EtOAc 5:1) to give 1.5 g (2.5 mmol) of the title compound as an off-white solid as a 1.7:1 (1st diastereomer: 2nd diastereomer) mixture of diastereomers.

Workup

  1. washthe flask was washed with N,N-dimethylformamide (2 ml)
  2. stirringThe resulting green solution was stirred at 120° C. for 17 hrs
  3. concentrationThe mixture was concentrated under reduced pressure (20 mbar, 70° C. bath temperature)
  4. customThe residue was purified by flash chromatography on silica gel (toluene→toluene/EtOAc 5:1)

Sources & evidence

ORD record
ord-96ca13f07f5d4ba483c2571d6a6c26e9
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

Loading…