Chloride → HCID 178432787, compound

HRID 1888339Notes

Reaction equation

HRID 1888339 reaction equation
N12CCCN=C1CCCCC2.[CH3:12][C:13]1[N:18]2[N:19]=[C:20]([CH2:22][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:21]=[C:17]2[C:16]([CH3:42])=[N:15][CH:14]=1.[Cl-].[C:44]1([C:50]2[NH:51][CH:52]=[C:53]([CH:55]=O)[N:54]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[CH3:12][C:13]1[N:18]2[N:19]=[C:20]([CH2:22][CH2:55][C:53]3[N:54]=[C:50]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[NH:51][CH:52]=3)[N:21]=[C:17]2[C:16]([CH3:42])=[N:15][CH:14]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59151223(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphoniumHCID 178519858HCID 178519858, compound

Product 1

HCID 178432787HCID 178432787, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.087 mL, 0.58 mmol) was added to a stirred suspension of (5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium; chloride (0.27 g, 0.58 mmol) and 2-Phenyl-1H-imidazole-4-carbaldehyde (0.100 g, 0.581 mmol) in dry THF (8 mL) and the mixture was stirred at room temperature under an atmosphere of Argon overnight. Some solid was filtered off and the solvent was removed in vac. The remanens was dissolved in DCM, and purified by silica gel chromatography (Eluent: 0-100% EtOAc in n-heptane). Yield: 97 mg of the intermediate as a cis/trans mixture as an oil (53%).

Workup

  1. filtrationSome solid was filtered off
  2. customthe solvent was removed in vac
  3. dissolutionThe remanens was dissolved in DCM
  4. custompurified by silica gel chromatography (Eluent: 0-100% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-0c9a40b8dc8c40bb89a98c47aa1d5812
Source dataset
uspto-grants-2013_08
Patent number
US08501797B2

Reaction notes

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