N,N-Diethylethylenediamine → HCID 12112112, 화합물

HRID 480194

반응식

HRID 480194 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.C(O)(=O)C.ClC(Cl)C.[CH2:38]([N:40]([CH2:43][CH2:44][NH2:45])[CH2:41][CH3:42])[CH3:39].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH2:7][NH:45][CH2:44][CH2:43][N:40]([CH2:41][CH3:42])[CH2:38][CH3:39])[CH:9]=1

참가 물질

7

반응물 5

HCID 60993N,N-DiethylethylenediamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18768099HCID 18768099, 화합물HCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

생성물 1

HCID 12112112HCID 12112112, 화합물수율 30.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.100 g, 0.25 mmol) in 10:1 dichloroethane acetic acid (2.2 mL) was added (diethylamino)ethylamine (0.088 mL, 0.625 mmol) and the resulting solution was stirred for 1 hour at ambient temperature. To this was added sodium cyanoborohydride (0.0094 g, 0.15 mmol) and the reaction was stirred overnight at ambient temperature. Upon completion water was added and the mixture was basified with solid sodium bicarbonate (pH>10). The product was extracted with dichloromethane (2×) and diethyl ether (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.039 g, x 30% yield)

후처리

  1. stirringthe reaction was stirred overnight at ambient temperature
  2. extractionThe product was extracted with dichloromethane (2×) and diethyl ether (2×)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dba56af168444ddabdea68328ee57ade
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649611B2

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