Sodium hydride → HCID 66585065, 화합물

HRID 2368986노트

반응식

HRID 2368986 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 66585065HCID 66585065, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6898de6c93bc41e88c3f6cc9c19c8c26
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703784B2

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