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

HRID 333741Notes

Reaction equation

HRID 333741 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:49]2[N:53]([CH3:54])[N:52]=[CH:51][CH:50]=2)=[N:40][N:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[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>[CH3:56][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:36][C:37]1[C:38](=[O:55])[C:39]([C:49]2[N:53]([CH3:54])[N:52]=[CH:51][CH:50]=2)=[N:40][N:41]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:42]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 45852153-(1-Methyl-1H-benzimidazol-2-yl)propan-1-olHCID 895867585-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 895864715-[3-(1-methyl-1H-benzimidazol-2-yl)propoxy]-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-oneYield 49.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (20 mL) was added to di-tert-butyl diazene-1,2-dicarboxylate (345 mg), and triphenylphosphine (459 mg) and the mixture was stirred at room temperature for 10 min. Then, 5-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one (268 mg), and further, 3-(1-methyl-1H-benzimidazol-2-yl)propan-1-ol (285 mg) were added, and the mixture was stirred at room temperature for 64 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 (217 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 64 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-85e1babd8d854cf1b6ede54fcdd2f9d4
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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