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Dimethylamine → 4-(6-Dimethylamino-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 967415
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HRID 967415 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17](Cl)[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][NH:26][CH3:27]>CO.C(Cl)Cl.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([N:26]([CH3:27])[CH3:25])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 2

HCID 674DimethylamineHCID 57500931Tert-butyl 4-[(6-chloro-3-nitropyridin-2-yl)amino]piperidine-1-carboxylate

생성물 1

HCID 691571204-(6-Dimethylamino-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester수율 104.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226129Dichloromethane methanol
용매

실험 절차

To a stirring solution of 6 g (0.016 mol) of 4-(6-chloro-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester in MeOH/CH2Cl2 (84 mL/15 mL) was added 2.2 g (0.05 mol) of dimethylamine in THF (25 mL). The reaction mixture was stirred at room temperature for 16 h, and was then concentrated. The crude product was then dissolved in CH2Cl2 (400 mL) and washed with saturated NaHCO3 (2×200 mL). The washes were combined and extracted with EtOAc (100 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford 6.1 g (99%) of the desired product as a bright yellow solid. MS (electrospray): exact mass calculated for C17H27N5O4, 365.21; m/z found, 388.19 [M+Na]+. 1H NMR (400 MHz, CDCl3): 8.74 (d, J=7.07 Hz, 1H), 8.18 (d, J=9.4 Hz, 1H), 5.97 (d, J=7.3 Hz, 1H), 4.28-4.16 (m, 1H), 4.07-3.93 (m, 2H), 3.17 (s, 6H), 3.01 (t, J=11.9 Hz, 2H), 2.05 (dd, J=12.4 Hz and 3.03 Hz, 2H), 1.60-1.50 (m, 2H), 1.47 (s, 9H).

후처리

  1. concentrationwas then concentrated
  2. dissolutionThe crude product was then dissolved in CH2Cl2 (400 mL)
  3. washwashed with saturated NaHCO3 (2×200 mL)
  4. extractionextracted with EtOAc (100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d040f54703ca4a55a8622be3bd143d62
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06953793B2

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