1,2-Dichloroethane → Cyclohexanecarboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 75621

반응식

HRID 75621 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH:10]1([C:16](O)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:16]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:17])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 199167865-Fluoro-2-hydrazinylpyridine

생성물 1

HCID 86686727Cyclohexanecarboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide수율 62%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 5-fluoro-2-hydrazinyl-pyridine (for reference procedure see WO 2010 022076, which is incorporated herein by reference in its entirety; 1.00 g, 7.87 mmol), cyclohexane carboxylic acid (1.21 g, 9.44 mmol), and HOBt.H2O (166 mg, 0.787 mmol) at 0° C. under N2 was added EDC (1.81 g, 9.44 mmol), then the mixture stirred at 0° C. for 15 min, and at RT for 17 h. Water was added, then the organics isolated, cooled to 0° C., then the resulting suspension filtered to leave the title compound as a white solid (1.16 g, 62%). 1H NMR (400 MHz, CDCl3): 1.21-1.38 (3H, m), 1.45-1.55 (2H, m), 1.66-1.73 (1H, m), 1.80-1.96 (4H, m), 2.22 (1H, tt, J 11.6, 3.5 Hz), 6.62-6.66 (2H, m), 7.29 (1H, ddd, J 9.2, 7.9, 3.1 Hz), 7.55 (1H, d, J=4.2 Hz), 8.03 (1H, d, J=2.9 Hz).

후처리

  1. waitat RT for 17 h
  2. temperaturethe organics isolated, cooled to 0° C.
  3. filtrationthe resulting suspension filtered

출처 및 근거

ORD 기록
ord-0438aecd2bd8479eb2f5017913471c2e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835431B2

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