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

HRID 1192601노트

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HRID 1192601 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-894e2314a37b480c8159f371c9f86779
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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