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Ammonium Acetate → 1-[8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanamine

HRID 1192534
ノート
印刷プレビュー

反応式

HRID 1192534 の反応式
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]([C:26](=O)[CH3:27])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:35].[Na+]>CO.C(#N)C>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]([CH:26]([NH2:35])[CH3:27])=[CH:17][C:18]([Cl:25])=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 583686451-[8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanone

生成物 1

HCID 583685251-[8-(4-{[tert-Butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanamine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6342
Acetonitrile
溶媒

反応条件

温度
65 °C

実験手順

A mixture of 1-[8-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-5-chloroquinolin-7-yl]ethanone (275 mg, 0.656 mmol) and ammonium acetate (506 mg, 6.56 mmol) in methanol (3.7 mL) and acetonitrile (3.7 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (82.5 mg, 1.31 mmol) was added to the resulting mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with sat. sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C22H35ClN3OSi (M+H)+: m/z=421.2; Found: 421.1.

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-54e384467a454e8c9dca4ff4170b8aaf
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680108B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート