Water → 4-[7-Methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]-piperidine-2-carboxylic acid methyl ester

HRID 388647ノート

反応式

HRID 388647 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=3)[CH:13]=2)[CH2:8][CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)=[O:4].O>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]([O:11][C:12]2[C:21]3[C:16](=[C:17]([CH3:24])[C:18]([O:22][CH3:23])=[CH:19][CH:20]=3)[N:15]=[C:14]([C:25]3[S:26][CH:27]=[C:28]([C:30]([F:31])([F:33])[F:32])[N:29]=3)[CH:13]=2)[CH2:8][CH2:7][NH:6]1)=[O:4]

参加物

4

反応物 2

HCID 962WaterHCID 66730320N-Cbz-{4-[7-methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]}-piperidine-2-carboxylic acid methyl ester

生成物 1

HCID 667303534-[7-Methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]-piperidine-2-carboxylic acid methyl ester収率 97%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
60 °C

実験手順

A mixture of compound 13 (1.08 g) in trifluoroacetic acid (17 mL) was stirred at 60° C. for 5 hrs. The solution was then cooled down at 0° C., water was added, and the mixture was extracted with EtOAc. Organics were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (DCM/MeOH) to yield compound 14 as a white powder in 97% yield. MS (ESI, EI+) m/z=482 (MH+).

後処理

  1. temperatureThe solution was then cooled down at 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. washOrganics were washed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by chromatography on silica gel (DCM/MeOH)

出典と根拠

ORDレコード
ord-422434a4f04e4bb6ac9d7b1da7a3392c
出典データセット
uspto-grants-2013_02
特許番号
US08377962B2

反応ノート

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