1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide

HRID 1177883ノート

反応式

HRID 1177883 の反応式
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH:13]=[N:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[O:50]=[C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:55][CH2:56]1)[CH2:48][NH:47][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([C:14]2[CH:13]=[N:12][CH:11]=[N:10][CH:15]=2)=[CH:24][CH:23]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 41872474-(Pyrimidin-5-yl)benzoic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

生成物 1

HCID 59559651N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide収率 31.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (185 mg, 0.24 mL, 1.1 mmol) was added to a stirred solution of 4-pyrimidin-5-yl-benzoic acid (85 mg, 0.42 mmol) in DMF (2 mL). HOBT (75 mg, 0.46 mmol) and EDCI (98 mg, 0.46 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (165 mg, 0.46 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent) to afford 65 mg (31% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide. LCMS Purity: 97%. 1H NMR (CDCl3): δ 9.2 (s, 1H), 9.0 (s, 2H), 8.0 (dd, 2H), 7.56 (d, 1H), 7.65 (m, 4H), 7.35 (m, 2H), 4.35 (m, 1H), 4.25 (m, 1H), 4.0 (m, 2H), 3.7 (m, 2H), 3.6 (m, 2H), 3.42 (m, 1H), 3.25 (m, 2H).

後処理

  1. filtrationfiltered the residue
  2. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent)

出典と根拠

ORDレコード
ord-22f63a14c08a43ea99c83443959fe478
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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