2-Fluorobenzoic acid → N-biphenyl-4-yl-3-[4-(2-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide

HRID 1665605ノート

反応式

HRID 1665605 の反応式
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.Cl.[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52](=[O:59])[N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:45][CH:44]=1>CN(C=O)C.O>[C:43]1([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:44]=[CH:45][C:46]([NH:49][C:50](=[O:60])[CH2:51][C:52]([N:53]2[CH2:54][CH2:55][N:56]([C:23](=[O:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[F:20])[CH2:57][CH2:58]2)=[O:59])=[CH:47][CH:48]=1

参加物

8

反応物 5

HCID 99352-Fluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66625265N-Biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride

生成物 1

HCID 44231081N-biphenyl-4-yl-3-[4-(2-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide収率 97.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

HOBt (34 mg, 0.25 mmol) and DIPEA (67.9 mg, 0.51 mmol) were added to a stirred solution of 2-fluorobenzoic acid (29 mg, 0.21 mmol) in DMF (1.5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (48 mg, 0.25 mmol) followed by N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (75 mg, 0.2 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water. The resulting precipitate was dried to afford 87 mg (94%) of N-biphenyl-4-yl-3-[4-(2-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide. LCMS: 446.18 (M+1)+ 93.2%, 1H NMR: (CDCl3): δ 9.7 (d, 1H), 7.6 (m, 6H), 7.44 (t, 4H), 7.34 (t, 1H), 7.22 (m, 1H), 7.14 (t, 1H), 3.86 (m, 6H), 3.54 (d, 2H), 3.4 (bs, 2H).

後処理

  1. additionwere added
  2. customThe resulting precipitate was dried

出典と根拠

ORDレコード
ord-70ce52a7bcb1407aba85d82456df6702
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

読み込み中…