Acetic Acid → Tert-Butyl 4-(3-(Isopropylamino)Pyridin-2-Yl)Piperazine-1-Carboxylate

HRID 864381노트

반응식

HRID 864381 반응식
[CH3:1][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].[CH3:21][C:22]([CH3:24])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:3][C:2]([CH3:20])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:18]([NH:19][CH:22]([CH3:24])[CH3:21])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 180Acetone2회HCID 2756375tert-Butyl 4-(3-aminopyridin-2-yl)piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride2회

생성물 1

HCID 10448702Tert-Butyl 4-(3-(Isopropylamino)Pyridin-2-Yl)Piperazine-1-Carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

1-[1,1-Dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication 88/08424, 2.0 g) is dissolved in 35 ml of methanol and acetone (0.48 g) is added. The reaction is cooled to 0° and acetic acid (to pH 4.0) is added. The reaction is stirred 15 min at 0° and then sodium cyanoborohydride (0.50 g) is added. The reaction is allowed to warm slowly to 20°-25° and followed by TLC until completion. Additional acetic acid, sodium cyanoborohydride and acetone are sometimes necessary to force the reaction to completion. The reaction is diluted with chloroform (100 ml), washed with saturated aqueous sodium bicarbonate (50 ml), saline (75 ml), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (75 g silica gel, 4:1 hexane/ethyl acetate) affords the title compound, NMR (300 MHz, CDCl3) 7.67, 6.91, 4.15, 3.57, 3.00, 1.48 and 1.23δ.

후처리

  1. temperatureThe reaction is cooled to 0°
  2. temperatureto warm slowly to 20°-25°
  3. customthe reaction to completion
  4. washwashed with saturated aqueous sodium bicarbonate (50 ml), saline (75 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (75 g silica gel, 4:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8df444984f4d48acacb27e39142e842a
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563142

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