Morpholine → 5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047162ノート

反応式

HRID 2047162 の反応式
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.O>[O:41]1[CH2:42][CH2:43][N:38]([C:2]2[CH:7]=[C:6]([N:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:15])([CH3:14])[CH3:16])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[N:5]3[N:25]=[CH:26][C:27]([C:28]4[CH:29]=[N:30][C:31]5[C:36]([CH:37]=4)=[CH:35][CH:34]=[CH:33][CH:32]=5)=[C:4]3[N:3]=2)[CH2:39][CH2:40]1

参加物

6

反応物 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

生成物 1

HCID 667335175-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine収率 82.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

A mixture of 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (77.9 mg, 0.14 mmoL), morpholine (36.7 mg, 0.42 mmoL), NaHCO3 (53 mg, 0.63 mmoL) in NMP (3 mL) was heated at 130° C. overnight. The mixture was cooled to room temperature and diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation of solvent afforded the crude displacement compound. Purification by column chromatography afforded 5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (70 mg, 82%). LCMS tR=2.72 Min (5 min run, UV254nm). Mass calculated for, M+ 606.3, observed LC/MS m/z 607.2 (M+H).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customEvaporation of solvent
  6. customafforded the crude displacement compound
  7. customPurification by column chromatography

出典と根拠

ORDレコード
ord-57361cf6508442c6bd37b8b45e0a1768
出典データセット
uspto-grants-2013_11
特許番号
US08591943B2

反応ノート

読み込み中…