Trifluoroacetic acid → HCID 68325413、化合物

HRID 2403304ノート

反応式

HRID 2403304 の反応式
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][N:22]=3)=[C:16]([F:30])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O>C(#N)C.O>[CH2:28]([O:27][C:24]1[CH:23]=[N:22][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:15][C:16]=2[F:30])=[N:26][CH:25]=1)[CH3:29]

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 68325477HCID 68325477、化合物

生成物 1

HCID 68325413HCID 68325413、化合物収率 109.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (12 mg) in acetonitrile (1.5 ml) and water (3 ml) was added trifluoroacetic acid (22.0 μl). The reaction mixture was then capped and the mixture was shaken at 80° C. for 3.5 h. The reaction mixture was then cooled to room temperature and poured into EtOAc and washed with 1 M aq. NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to afford (RS)-(5-ethoxy-pyrimidin-2-yl)-(2-fluoro-4-morpholin-2-yl-phenyl)-amine (10 mg, quant.) as an off-white solid. MS (ISP): 319.2 ([ M+H]+).

後処理

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with 1 M aq. NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH)

出典と根拠

ORDレコード
ord-20e75ec08fe243eea03ff6635fba3b15
出典データセット
uspto-grants-2014_08
特許番号
US08802673B2

反応ノート

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