Sodium ethoxide → HCID 69481040, 화합물

HRID 2364530노트

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HRID 2364530 반응식
[CH:1]1([N:4]([C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]2[C:6]([C:19]([O:21]C)=O)=[N:7][CH:8]=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=2)[CH2:3][CH2:2]1.[O-]CC.[Na+]>C(O)C>[CH:1]1([N:4]2[C:5]3[C:6](=[N:7][CH:8]=[C:9]([CH2:11][C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH:10]=3)[C:19]([OH:21])=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]2=[O:30])[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 2723922Sodium ethoxideHCID 69480475Methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

생성물 1

HCID 69481040HCID 69481040, 화합물수율 98%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of methyl 3-{cyclopropyl[3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (402 mg, 0.97 mmol) in ethanol (20 mL) at 0° C. was treated with sodium ethoxide (165 mg, 2.4 mmol). The reaction mixture was allowed to warm to room temperature as the bath warmed overnight. Solvents were removed in vacuo and the residue was taken up in water. The pH was adjusted to ˜5 with 1 N HCl (aq) and the aqueous layer extracted with ethyl acetate. The organics were dried over sodium sulfate filtered and concentrated to give ethyl 1-cyclopropyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (362 mg, 98%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=1.6 Hz, 1 H), 7.78 (s, 1 H), 7.18 (dd, J=8.7, 5.4 Hz, 2 H), 7.04 (t, J=8.7 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.13 (s, 2 H), 2.77 (m, 1 H), 1.46 (t, J=7.3 Hz, 3 H), 1.22 (m, 2 H), 0.76 (m, 2 H); MS m/z 383 (M+1).

후처리

  1. temperaturewarmed overnight
  2. customSolvents were removed in vacuo
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1f0de86dc7cd404f817e7b0afb071e09
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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