Ammonium Acetate → 1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]pyrrolidine-3-carbonitrile

HRID 1192601ノート

反応式

HRID 1192601 の反応式
[C:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:21])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[NH2:28][CH:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:21])[CH:5]=1)[CH3:2]

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 583686301-(7-Acetyl-5-chloroquinolin-8-yl)pyrrolidine-3-carbonitrile

生成物 1

HCID 583684901-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]pyrrolidine-3-carbonitrile

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-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidine-3-carbonitrile (0.016 g, 0.053 mmol) and ammonium acetate (0.0411 g, 0.534 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.010 g, 0.16 mmol) was added. The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C16H18ClN4 (M+H)+: m/z=301.1; Found: 301.1.

後処理

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperatureThe mixture was cooled to room temperature
  4. customquenched with sat. NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-894e2314a37b480c8159f371c9f86779
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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