Triphenylphosphine → 1-methyl-5-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333728Notes

Reaction equation

HRID 333728 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:36][C:37]1[C:38](=[O:55])[C:39]([C:44]2[N:48]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:47]=[CH:46][CH:45]=2)=[N:40][N:41]([CH3:43])[CH:42]=1.[CH3:56][N:57]1[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=2[N:59]=[C:58]1[CH2:66][CH2:67][CH2:68]O>C1(C)C=CC=CC=1>[CH3:43][N:41]1[CH:42]=[C:37]([O:36][CH2:68][CH2:67][CH2:66][C:58]2[N:57]([CH3:56])[C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=3[N:59]=2)[C:38](=[O:55])[C:39]([C:44]2[N:48]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:47]=[CH:46][CH:45]=2)=[N:40]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 45852153-(1-Methyl-1H-benzimidazol-2-yl)propan-1-olHCID 895867365-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Product 1

HCID 895865821-methyl-5-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (10 mL) was added to di-tert-butyl diazene-1,2-dicarboxylate (173 mg) and triphenylphosphine (229 mg) and the mixture was stirred at room temperature for 10 min. Then, 5-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (154 mg), 3-(1-methyl-1H-benzimidazol-2-yl)propan-1-ol (143 mg) were further added and the mixture was stirred at room temperature for 22 hr. The crystals precipitated from the reaction mixture were collected by filtration, washed successively with toluene, methanol and diisopropyl ether, and dried to give the title compound (134 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 22 hr
  2. customThe crystals precipitated from the reaction mixture
  3. filtrationwere collected by filtration
  4. washwashed successively with toluene, methanol and diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-bcef55f20ac74530ad241b2319e8b2ec
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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