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 1477709ノート

反応式

HRID 1477709 の反応式
[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

参加物

6

反応物 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、化合物

生成物 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)-one収率 2.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-4309dd9c10694831b8bba1f30c6e690b
出典データセット
uspto-grants-2016_08
特許番号
US09403798B2

反応ノート

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