Water → Methyl 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

HRID 2364528노트

반응식

HRID 2364528 반응식
[CH:1]1([NH:4][C:5]2[C:6]([C:19]([OH:21])=[O:20])=[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.[C:22](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]2[C:6]([C:19]([O:21][CH3:22])=[O:20])=[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)[CH2:2][CH2:3]1

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 694804773-(Cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylic acid

생성물 1

HCID 69481047Methyl 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate수율 77%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylic acid (298 mg, 1.1 mmol) in DMF (10 mL) was added potassium carbonate (316 mg, 2.3 mmol) followed by methyl iodide (0.15 mL, 2.3 mmol). The resultant suspension was stirred for 1.5 hours at which time water and ethyl acetate were added. The layers were separated and the organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over sodium sulphate. Filtration and concentration followed by purification by silica gel chromatography provided methyl 3-(cyclopropylamino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (234 mg, 77%) as a white crystalline solid upon standing. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=1.9 Hz, 1 H), 7.78 (br, 1 H), 7.24 (s, 1 H), 7.15 (dd, J=8.5, 5.4 Hz, 2 H), 7.00 (t, J=8.7 Hz, 2 H), 3.96 (s, 2 H), 3.93 (s, 3 H), 2.39 (m, 1 H), 0.77 (m, 2 H), 0.52 (m, 2 H); MS m/z 301 (M+1).

후처리

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organics were dried over sodium sulphate
  6. filtrationFiltration and concentration
  7. customfollowed by purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-863cb6821c464aaf8f68a4a4ff02bf87
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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