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 1477709노트

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HRID 1477709 반응식
[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

참가 물질

6

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724700Benzotriazol-1-yl-oxytripyrrolidinophosphoniumHCID 34348855-Fluoro-1H-benzo[d]imidazole-2(3H)-thioneHCID 178518532HCID 178518532, 화합물

생성물 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)-one수율 2.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-4309dd9c10694831b8bba1f30c6e690b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403798B2

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