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Triphosgene → 1-(4-(Trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea

HRID 1505182
ノート
印刷プレビュー

反応式

HRID 1505182 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])[O:23][C:24](Cl)(Cl)Cl)Cl.[N-:30]=[C:31]=[O:32]>CCOC(C)=O.CN(C=O)C>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:31]([NH:30][C:6]2[C:9]3[NH:10][C:22](=[O:28])[O:23][C:24]=3[CH:3]=[CH:4][CH:5]=2)=[O:32])=[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

6

反応物 3

HCID 94429TriphosgeneHCID 105034IsocyanateHCID 58873466HCID 58873466、化合物

生成物 1

HCID 534762441-(4-(Trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea収率 20%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒
2 回

反応条件

温度
80 °C

実験手順

Amine 2b (289 mg, 1.2 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (356 mg, 1.2 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 1b (180 mg, 1.2 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). 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 100 mg of a white solid. Yield=20% 1HNMR (DMSO, 200 MHz) δ 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J=5.6 Hz), 6.55 (2H, dd, J=8.8 Hz, J′=1.2 Hz), 7.05 (1H, t, J=8.2 Hz), 7.17 (2H, d, J=7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 11.53 (1H, bs), 11.80 (1H, bs); [M+1] 421.2 (C20H19F3N4O3 requires 420.39).

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-87f4a6a49b314908bcf0068db0f5f31e
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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