1,2-Dichloroethane → 3-(3-fluoropyridin-2-yl)-N-[(1R)-1-(5-fluoropyridin-2-yl)ethyl]-5-(5-methylpyridin-2-yl)benzamide

HRID 888394노트

반응식

HRID 888394 반응식
[Cl-].[Na+].[F:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:18]=2)[C:13]([OH:15])=O)=[N:6][CH:7]=[CH:8][CH:9]=1.Cl.[F:27][C:28]1[CH:29]=[CH:30][C:31]([C@H:34]([NH2:36])[CH3:35])=[N:32][CH:33]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O>[F:3][C:4]1[C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[CH:18]=2)[C:13]([NH:36][C@@H:34]([C:31]2[CH:30]=[CH:29][C:28]([F:27])=[CH:33][N:32]=2)[CH3:35])=[O:15])=[N:6][CH:7]=[CH:8][CH:9]=1

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66690953(1R)-1-(5-fluoropyridin-2-yl)ethan-1-amine hydrochlorideHCID 684966373-(3-Fluoropyridin-2-yl)-5-(5-methylpyridin-2-yl)benzoic acid

생성물 1

HCID 252567493-(3-fluoropyridin-2-yl)-N-[(1R)-1-(5-fluoropyridin-2-yl)ethyl]-5-(5-methylpyridin-2-yl)benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the sodium chloride salt of 3-(3-fluoropyridin-2-yl)-5-(5-methylpyridin-2-yl)benzoic acid (25.0 mg, 0.05 mmol) in N,N-dimethylformamide (0.35 mL) were added (1R)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride salt (16.5 mg, 0.08 mmol), EDC (14.9 mg, 0.08 mmol), HOBT (7.92 mg, 0.05 mmol) and triethylamine (21.6 μL, 0.16 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, the mixture was cooled to ambient temperature. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound. HRMS 431.1706 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.73 (q, J=1.6 Hz, 1H); 8.57-8.54 (m, 2H); 8.52 (t, J=1.7 Hz, 1H); 8.45 (q, J=1.5 Hz, 1H); 8.44 (d, J=2.8 Hz, 1H); 7.78 (d, J=8.1 Hz, 1H); 7.62-7.52 (m, 3H); 7.43-7.31 (m, 3H); 5.43 (p, J=7.0 Hz, 1H); 2.40 (s, 3H); 1.61 (d, J=6.8 Hz, 3H).

후처리

  1. temperaturethe mixture was cooled to ambient temperature
  2. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-65f3273bed1647e9938f50ca54aad221
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

반응 노트

불러오는 중…