Sodium hydride → HCID 66585065、化合物

HRID 2368986ノート

反応式

HRID 2368986 の反応式
[H-].[Na+].Br[CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[O:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([NH2:25])[N:22]3[N:26]=[CH:27][C:28]([C:29]4[CH:30]=[N:31][C:32]5[C:37]([CH:38]=4)=[CH:36][CH:35]=[CH:34][CH:33]=5)=[C:21]3[N:20]=2)[CH2:15][CH2:14]1>CN(C=O)C.[NH4+].[Cl-]>[O:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:24]=[C:23]([NH:25][CH2:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[N:22]3[N:26]=[CH:27][C:28]([C:29]4[CH:30]=[N:31][C:32]5[C:37]([CH:38]=4)=[CH:36][CH:35]=[CH:34][CH:33]=5)=[C:21]3[N:20]=2)[CH2:17][CH2:18]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 256128tert-Butyl 3-bromopropionateHCID 581733995-Morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

生成物 1

HCID 66585065HCID 66585065、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

実験手順

NaH (25.1 mg, 60%, 0.63 mmol) and then tert-butyl 3-bromopropanoate (69.7 uL, 0.42 mmoL) was added to 5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (72.3 mg, 0.21 mmoL) in DMF (3 mL). The mixture was stirred at room temperature until LCMS indicated complete conversion. The reaction mixture was diluted with Sat. NH4Cl 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 tert-butyl 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-ylamino)propanoate. The crude ester was heated with 4N HCl (4 mL) and 1,4-dioxane (4 mL) at 50° C. for 3 h. Concentration provided 3-(5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-ylamino)propanoic acid. LCMS tR=1.10 Min (5 min run, UV254nm). Mass calculated for, M+ 418.1, observed LC/MS m/z 419.2 (M+H).

後処理

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation of solvent

出典と根拠

ORDレコード
ord-6898de6c93bc41e88c3f6cc9c19c8c26
出典データセット
uspto-grants-2014_04
特許番号
US08703784B2

反応ノート

読み込み中…