Triphenylphosphine → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1078342

Reaction equation

HRID 1078342 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:40]2[NH:44][NH:43][C:42](=[O:45])[CH2:41]2)[CH:35]=[CH:36][C:37]=1[O:38][CH3:39].[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH2:56][CH2:57][N:58]([CH2:60][CH2:61][CH2:62]O)[CH3:59])[CH:51]=[CH:52][C:53]=1[O:54][CH3:55]>O1CCCC1.C1(C)C=CC=CC=1.CN(C)C=O>[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH2:56][CH2:57][N:58]([CH2:60][CH2:61][CH2:62][O:45][C:42]2[CH:41]=[C:40]([C:34]3[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:32]([O:31][CH3:30])[CH:33]=3)[NH:44][N:43]=2)[CH3:59])[CH:51]=[CH:52][C:53]=1[O:54][CH3:55]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 152835213-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)amino]-propanolHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-oneHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 152835203-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazoleYield 50.6%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1.31 g of triphenylphosphine were dissolved in 15 ml of tetrahydrofuran. 1.6 ml of a solution of 0.8 ml of ethyl azodicarboxylate in 0.8 ml of toluene were added dropwise to the solution at a temperature of 5° C. After 5 minutes a solution of 1.1 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one in 10 ml of dimethylformamide was added dropwise. After 20 minutes a solution of 1.26 g of 3-[N-(2-(3,4-dimethoxyphenyl)-ethyl)-N-methylamino]-propanol in 10 ml of tetrahydrofuran was added dropwise. The reaction mixture was subsequently stirred at 20° C. for 48 hours. The reaction mixture was then evaporated to dryness. The resulting crude product was purified by flash chromatography in accordance with the method described in Example 1 E). 1.14 g of the title compound were obtained as an oily base. This base was converted as described in Example 1 E), to the hydrochloride having a melting point of from 189° to 192° C.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customThe resulting crude product was purified by flash chromatography in accordance with the method

Sources & evidence

ORD record
ord-576124c74dab4f82971ae826d2f08197
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Linked notes

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