Ammonium Acetate → 1-{5-Chloro-8-[(3S)-3-fluoropyrrolidin-1-yl]quinolin-7-yl}ethanamine

HRID 1192597ノート

反応式

HRID 1192597 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][C@H:17]([F:20])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:27])[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][C@H:17]([F:20])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368449HCID 58368449、化合物

生成物 1

HCID 583685801-{5-Chloro-8-[(3S)-3-fluoropyrrolidin-1-yl]quinolin-7-yl}ethanamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

A mixture of 1-{5-chloro-8-[(3S)-3-fluoropyrrolidin-l-yl]quinolin-7-yl}ethanone (0.10 g, 0.34 mmol) and ammonium acetate (0.263 g, 3.42 mmol) in methanol (1.5 mL) and acetonitrile (1.5 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.064 g, 1.0 mmol). The reaction was heated at 65° C. overnight, cooled to room temperature and quenched with sat. NaHCO3 solution and extracted with Ethyl acetate. The combined organic layers were dried over MgSO4, concentrated and purified on a preparative LCMS (pH=10) to give the desired product. LCMS calculated for C15H18ClFN3 (M+H)+: m/z=294.1; Found: 294.0.

後処理

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperaturecooled to room temperature
  4. customquenched with sat. NaHCO3 solution
  5. extractionextracted with Ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. custompurified on a preparative LCMS (pH=10)

出典と根拠

ORDレコード
ord-4a1a84bb0d614468b185618de32397be
出典データセット
uspto-grants-2014_03
特許番号
US08680108B2

反応ノート

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