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Sodium Bicarbonate → Tert-butyl 4-(((4-methyl-5-phenyl-4h-1,2,4-triazol-3-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

HRID 628695
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HRID 628695 반응식
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[CH:13]=O.[N:15]1[C:24]2[CH:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CC(O)=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[C:3]1[CH2:13][N:25]([CH:23]1[C:24]2[N:15]=[CH:16][CH:17]=[CH:18][C:19]=2[CH2:20][CH2:21][CH2:22]1)[CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34]
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참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 115428934-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehydeHCID 42609132558446-23-4

생성물 1

HCID 59176412Tert-butyl 4-(((4-methyl-5-phenyl-4h-1,2,4-triazol-3-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate

시약·촉매·용매 2

HCID 176
Acetic Acid
촉매
HCID 111,2-Dichloroethane용매

반응 조건

온도
65 °C

실험 절차

To a solution of 4-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehyde, 36, (0.41 g, 2.20 mmol) in 1,2-dichloroethane (4 mL) was added tert-butyl 4-(5,6,7,8-tetrahydroquinolin-8-ylamino)butylcarbamate, 3, (0.76 g, 2.40 mmol), sodium triacetoxyborohydride (0.84 g, 3.95 mmol), and AcOH (10 drops). The reaction mixture was heated to 65° C. and stirred for 18 h. The reaction mixture was cooled to room temperature and poured into saturated aqueous NaHCO3 (15 mL) and extracted with ethyl acetate (2×10 mL). The combined organic phases were washed with brine then dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane) to yield 37: 1H NMR (400 MHz, CDCl3) δ 8.40, (d, J=5.2 Hz, 1H), 7.60-7.57 (m, 2H), 7.48-7.44, (m, 3H), 7.31, (d, J=7.2 Hz, 1H), 7.0, (dd, J=8.0, 5.2 Hz, 1H), 5.01, (bs, 1H), 4.20-3.92, (m, 3H), 3.20-2.60, (m, 6H), 2.20-1.85, (m, 4H), 1.75-1.30 (m, 13H); ESI+ MS: m/z (rel intensity) 491 (100, M+H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-6a711fde75cb4621950b822d7447ce0f
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09314468B2

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