1-Hydroxybenzotriazole → Biphenyl-4-carboxylicacid {2-oxo-2-[4-(2,3,6-trifluoro-benzoyl)-piperazin-1-yl]-1-ethyl}-amide

HRID 1178102

反応式

HRID 1178102 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]1[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:12]=1[C:13]([OH:15])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[O:44]=[C:45]([N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)[CH2:46][NH:47][C:48]([C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)=[O:49]>CN(C=O)C.O>[O:44]=[C:45]([N:62]1[CH2:67][CH2:66][N:65]([C:13](=[O:15])[C:12]2[C:16]([F:21])=[CH:17][CH:18]=[C:19]([F:20])[C:11]=2[F:10])[CH2:64][CH2:63]1)[CH2:46][NH:47][C:48]([C:50]1[CH:51]=[CH:52][C:53]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[CH:54][CH:55]=1)=[O:49]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5200622,3,6-Trifluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

生成物 1

HCID 57855662Biphenyl-4-carboxylicacid {2-oxo-2-[4-(2,3,6-trifluoro-benzoyl)-piperazin-1-yl]-1-ethyl}-amide収率 36.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (149.8 mg, 1.15 mmol) was added to a stirred solution of 2,3,6-trifluoro-benzoic acid (45.3 mg, 0.26 mmol) in DMF (3 mL), HOBt (38.2 mg, 0.28 mmol) and EDCI.HCl (123.4 mg, 0.64 mmol) at room temperature. After 2 minutes biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide (100 mg, 0.31 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, and the resulting precipitate was filtered. The residue was purified by column chromatography (using 60-120 mesh silica gel and 60% EtOAc in hexane as eluent) to afford 45 mg (36.2% yield) of biphenyl-4-carboxylicacid {2-oxo-2-[4-(2,3,6-trifluoro-benzoyl)-piperazin-1-yl]-ethyl}-amide, LC-MS purity: 92.11%, 1H NMR: (DMSO) δ 7.97-7.9 (d, 2H), 7.74-7.6 (q, 4H), 7.52-7.44 (t, 2H), 7.44-7.36 (m, 1H), 7.36-7.28 (m, 1H), 7.02-6.92 (m, 1H), 4.4-4.26 (dd, 2H), 3.98-3.82 (m, 3H), 3.78-3.72 (t, 1H), 3.68-3.62 (t, 1H), 3.58-3.52 (m, 1H), 3.48-3.38 (m, 2H).

後処理

  1. filtrationthe resulting precipitate was filtered
  2. customThe residue was purified by column chromatography (using 60-120 mesh silica gel and 60% EtOAc in hexane as eluent)

出典と根拠

ORDレコード
ord-983fe6142fa341278bbdea08969bdbf2
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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