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Methanol → 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea

HRID 1505157
ノート
印刷プレビュー

反応式

HRID 1505157 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1.ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.[N-:30]=[C:31]=O.CO.[CH3:35][N:36]([CH:38]=[O:39])C>CCOC(C)=O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:38]([NH:36][C:35]2[C:31]3[NH:30][C:22](=[O:28])[NH:10][C:9]=3[CH:6]=[CH:5][CH:4]=2)=[O:39])=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 94429TriphosgeneHCID 105034IsocyanateHCID 58873466HCID 58873466、化合物

生成物 1

HCID 534773861-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea収率 20%

試薬・触媒・溶媒

1
HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

Amine 2b (0.5 ml, 2 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (580 mg, 2 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (296 mg, 1.99 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 170 mg of a yellow solid. Yield=20% 1HNMR (DMSO, 400 MHz) δ 1.91 (4H, bs), 3.22 (4H, bs), 4.38 (2H, d, J=5.2 Hz), 6.62 (1H, d, J=8 Hz), 6.72 (1H, t), 6.83 (1H, t), 6.95 (1H, d, J=8 Hz), 7.08 (1H, s), 7.18 (1H, d, J=7.6 Hz), 7.45 (1H, d, J=7.6 Hz), 8.35 (1H, bs), 9.98 (1H, bs), 10.60 (1H, bs); [M+1] 420.18 (C20H20F3N5O2 requires 419.4).

後処理

  1. additionwas added to the solution
  2. customthen evaporated
  3. dissolutionthe residue was dissolved in 5 ml of DMF
  4. temperaturethe mixture was warmed at 80° C. for 8 hours
  5. customThe solvent was evaporated
  6. dissolutionthe crude was dissolved in AcOEt (30 ml)
  7. washwashed with water (1×20 ml) and brine
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe purification of the crude residue by chromatographic column

出典と根拠

ORDレコード
ord-263a8144649f44bb9e569f3f76882ec5
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09216975B2

反応ノート

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