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Triphosgene → 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-5-yl)urea

HRID 1505191
ノート
印刷プレビュー

反応式

HRID 1505191 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)(OC(=O)OC(Cl)(Cl)Cl)Cl.[N-:30]=[C:31]=[O:32].N[C:34]1[C:43]2[NH:42][C:41](=[O:44])[CH2:40][O:39][C:38]=2[CH:37]=[CH:36][CH:35]=1>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:34]2[C:43]3[NH:42][C:41](=[O:44])[CH2:40][O:39][C:38]=3[CH:37]=[CH:36][CH:35]=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

7

反応物 4

HCID 94429TriphosgeneHCID 105034IsocyanateHCID 107970995-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 58873466HCID 58873466、化合物

生成物 1

HCID 534763601-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-5-yl)urea収率 21%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

Amine 2b (471 mg, 1.94 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (576 mg, 1.94 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 1e (213 mg, 1.3 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 120 mg of a white solid. Yield=21% 1HNMR (DMSO, 400 MHz) δ 1.91 (4H, m), 3.21 (4H, m), 4.48 (2H, d, J=6 Hz), 4.63 (2H, s), 6.64 (2H, dd, J=10.8 Hz, J′=8 Hz), 6.88 (1H, t, J=8 Hz), 7.12 (1H, s), 7.19 (1H, d, J=8.8 Hz), 7.34 (1H, d, J=8 Hz), 8.63 (1H, t), 10.68 (1H, bs), 10.90 (1H, bs); [M+1] 435.2 (C21H21F3N4O3 requires 434.4).

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-9a8ed421d50149319c4339aa6e3c097e
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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