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Dichloromethane → HCID 42637837, 화합물

HRID 2364229
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HRID 2364229 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.Cl[C:26](=[O:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].ClCCl.C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][C:26]([N:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:11]1[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][CH:14]=[C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:10]=1)=[O:33])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 69482102HCID 69482102, 화합물

생성물 1

HCID 42637837HCID 42637837, 화합물수율 55%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of ethyl 5-[(4-fluorophenyl)methyl]-3-3-[(2-methylpropyl)amino]-3-2-pyridinecarboxylate and ethyl 5-[(4-fluorophenyl)methyl]-3-[(2-methyl-1-propen-1-yl)amino]-2-pyridinecarboxylate (˜1.7:1 mixture, 419 mg, 1.3 mmol) in 1,2-dichloroethane (15 mL) was added ethyl 3-chloro-3-oxopropanoate (0.25 mL, 90%, 1.9 mmol). The resultant solution was heated at 85° C. for 5 hours. Upon cooling to room temperature, dichloromethane and saturated aqueous sodium bicarbonate were added and the layers separated. The organic layer was washed with brine. The aqueous layers were extracted with dichloromethane and the combined organics dried over sodium sulfate. Filtration and concentration followed by silica gel chromatography provided ethyl 3-[[3-(ethyloxy)-3-oxopropanoyl](2-methylpropyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (309 mg, 55%). 1H NMR (CDCl3) δ 8.56 (s, 1 H), 7.45 (s, 1 H), 7.10 (m, 2 H), 6.99 (m, 2 H), 4.39 (q, J=7.2 Hz, 2 H), 4.02-3.97 (m, 5 H), 3.15 (d, J=15.6 Hz, 1 H), 3.04 (d, J=15.6 Hz, 1 H), 2.81 (dd, J=13.6, 6.0 Hz, 1 H), 1.62 (m, 1 H), 1.36 (t, J=7.2 Hz, 3 H), 1.16 (t, J=6.8 Hz, 3 H), 0.90 (d, J=6.4 Hz, 3 H), 0.81 (d, J=6.4 Hz, 3 H); MS: m/z 445 (M+1). Further elution provided ethyl 3-[[3-(ethyloxy)-3-oxopropanoyl](2-methyl-1-propen-1-yl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (115 mg, 21%). 1H NMR (CDCl3) δ 8.37 (s, 1 H), 7.32 (s, 1 H), 7.07 (m, 2 H), 6.97 (m, 2 H), 6.15 (s, 1 H), 4.39 (q, J=7.2 Hz, 2 H), 4.18 (q, J=7.2 Hz, 2 H), 3.48 (s, 2 H), 1.70 (s, 3 H), 1.59 (s, 3 H), 1.38 (t, J=7.2 Hz, 3 H), 1.25 (t, J=7.2 Hz, 3 H); MS: m/z 445 (M+1).

후처리

  1. customthe layers separated
  2. washThe organic layer was washed with brine
  3. extractionThe aqueous layers were extracted with dichloromethane
  4. dry with materialthe combined organics dried over sodium sulfate
  5. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-63a8646e2885407bb7bb606c93503762
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691991B2

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