Ammonium Acetate → 1-[5-Chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanamine

HRID 1192552ノート

反応式

HRID 1192552 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17][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:29].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:29])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17][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 583685421-[5-Chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanone

生成物 1

HCID 583686671-[5-Chloro-8-(4,4-difluoropiperidin-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-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanone (20 mg, 0.06 mmol) and ammonium acetate (47.5 mg, 0.616 mmol) in methanol (0.35 mL) and acetonitrile (0.35 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (7.7 mg, 0.12 mmol) was added to the resulting mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude amine was used directly in the next step. LCMS calculated for C16H19ClF2N3 (M+H)+: m/z=326.1; Found: 326.0.

後処理

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-6c7d798b59c74a8c959dcb2eb85958b2
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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