Acetic Acid → Ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methylthio)propyl]amino}-2-pyridinecarboxylate

HRID 2364283노트

반응식

HRID 2364283 반응식
[NH2:1][C:2]1[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.[CH3:21][S:22][CH2:23][CH2:24][CH:25]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[F:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C:6]2[CH:7]=[C:2]([NH:1][CH2:25][CH2:24][CH2:23][S:22][CH3:21])[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][CH:5]=2)=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 18635MethionalHCID 5049666Sodium triacetoxyborohydrideHCID 42637772Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

생성물 1

HCID 69480921Ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methylthio)propyl]amino}-2-pyridinecarboxylate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (150 mg, 0.547 mmol) in 1,2 dichloroethane (2 mL) was added 3-(methythio)propionaldehyde (82 μL, 0.821 mmol), acetic acid (156 μL, 2.74 mmol), and sodium triacetoxyborohydride (232 mg, 1.09 mmol) respectively. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) provided ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methylthio)propyl]amino}-2-pyridinecarboxylate as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J=1.5 Hz, 1 H), 7.73 (t, J=5.1 Hz, 1 H), 7.11 (dd, J=8.4, 5.5 Hz, 2 H), 6.96 (t, J=8.6 Hz, 2 H), 6.82 (s, 1 H), 4.40 (q, J=7.1 Hz, 2 H), 3.90 (s, 2 H), 3.24 (m, 2 H), 2.58 (m, 2 H), 2.07 (s, 3 H), 1.90 (m, 2 H), 1.41 (t, J=7.1 Hz, 3 H); MS m/z 363 (M+H)+.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-c0c1c69d95f34fb99ad26da7c0547de6
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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