1H-Indazole → HCID 117839489, compound

HRID 1477699Notes

Reaction equation

HRID 1477699 reaction equation
CC1C=CC(S(O[CH2:12][N:13]2[CH:18]=[N:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[N:15][C:14]2=[O:32])(=O)=O)=CC=1.N12CCCN=C1CCCCC2.[NH:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[N:45]1>ClCCl>[N:44]1[N:45]([CH2:12][N:13]2[CH:18]=[N:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[N:15][C:14]2=[O:32])[CH:46]=[C:47]2[C:52]=1[CH:51]=[CH:50][CH:49]=[CH:48]2

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 117839573HCID 117839573, compound

Product 1

HCID 117839489HCID 117839489, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution of {4-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxo-1,3,5-triazin-1(2H)-yl}methyl 4-methylbenzenesulfonate (165 mg, 0.36 mmol) synthesized in Reference Synthesis Example 4, 1,8-diazabicyclo[5.4.0]undeca-7-ene (65 μL, 0.44 mmol) and 1H-indazole (43 mg, 0.40 mmol) were added at room temperature and the resultant mixture was stirred at room temperature for 30 minutes. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (8.5 mg, yield: 5.2%).

Workup

  1. additionwere added at room temperature
  2. customAfter the completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe resultant residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0a879fb888f54057afa8330bc33e3e68
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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