1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(4-Chlorobenzyl)-4-[4-(5-fluoro-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl]-1,3,5-triazin-2(1H)-one

HRID 1477709Notes

Reaction equation

HRID 1477709 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10](O)=[N:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[N:17]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:21]2C=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.N12CCCN=C1CCCCC2.[F:54][C:55]1[CH:64]=[CH:63][C:58]2[NH:59][C:60](=[S:62])[NH:61][C:57]=2[CH:56]=1>C(#N)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:17]3[CH2:23][CH2:24][CH:25]([N:59]4[C:58]5[CH:63]=[CH:64][C:55]([F:54])=[CH:56][C:57]=5[NH:61][C:60]4=[S:62])[CH2:20][CH2:21]3)=[N:9][C:8]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724700Benzotriazol-1-yl-oxytripyrrolidinophosphoniumHCID 34348856-fluoro-1H-benzimidazole-2-thiolHCID 178518532HCID 178518532, compound

Product 1

HCID 1178391761-(4-Chlorobenzyl)-4-[4-(5-fluoro-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl]-1,3,5-triazin-2(1H)-oneYield 2.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To an acetonitrile solution (1 mL) of 1-(4-chlorobenzyl)-4-hydroxy-1,3,5-triazin-2(1H)-one (20 mg, 0.08 mmol) synthesized in Reference Synthesis Example 10, (benzotriazol-1-yloxy)tripyrrolidino-phosphonium (47 mg, 0.10 mmol) and 1,8-diazabicyclo[5.4.0]undeca-7-ene (15 μL, 0.10 mmol) were added at room temperature and the resultant mixture was stirred for 20 minutes. To the reaction solution, 5-fluoro-1H-benzo[d]imidazole-2(3H)-thione (25 mg, 0.10 mmol) was added and the resultant reaction solution was stirred at 80° C. for 10 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 (chloroform/ethyl acetate=1/1 (v/v)) to obtain the title compound (0.8 mg, yield: 2.0%).

Workup

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

Sources & evidence

ORD record
ord-4309dd9c10694831b8bba1f30c6e690b
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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