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

HRID 888394ノート

反応式

HRID 888394 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-65f3273bed1647e9938f50ca54aad221
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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