Triphenylphosphine → HCID 67981111, compound

HRID 1520037Notes

Reaction equation

HRID 1520037 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[CH:17]=[CH:18][C:19](=[O:22])[NH:20][N:21]=1.O[CH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[N:29]=[C:28]2[C:41]1[N:42]=[N:43][N:44]([C:46]2[CH:51]=[CH:50][C:49]([C:52]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)=[O:53])=[CH:48][CH:47]=2)[CH:45]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[CH:18][C:19](=[O:22])[N:20]([CH2:24][C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35])[N:29]=[C:28]3[C:41]2[N:42]=[N:43][N:44]([C:46]3[CH:51]=[CH:50][C:49]([C:52]([N:54]4[CH2:59][CH2:58][O:57][CH2:56][CH2:55]4)=[O:53])=[CH:48][CH:47]=3)[CH:45]=2)[N:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2528286-Chloropyridazin-3-olHCID 5363146Diisopropyl azodicarboxylateHCID 67981415HCID 67981415, compound

Product 1

HCID 67981111HCID 67981111, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIAD (0.35 mL; 1.80 mmol; 2.3 eq.) was added dropwise over 1 min to a solution of 6-chloropyridazin-3(2H)-one (153 mg; 1.17 mmol; 1.5 eq.), tert-butyl 5-(hydroxymethyl)-3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole-1-carboxylate (393 mg; 0.78 mmol; 1.0 eq.) and triphenylphosphine (430 mg; 1.64 mmol; 2.1 eq.) in DCM (15 mL). The reaction mixture was stirred at RT for 16 h, then diluted with DCM and sequentially washed with a 1N HCl solution and brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (EtOAc: n-heptane, gradient from 30:70 to 90:10) to give the title compound as a white solid (316 mg, 66%).

Workup

  1. washsequentially washed with a 1N HCl solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by flash chromatography on silica (EtOAc: n-heptane, gradient from 30:70 to 90:10)

Sources & evidence

ORD record
ord-8a18135896dc460aa43d733b944e1f3e
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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