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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,4-Difluoro-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177891
ノート
印刷プレビュー

反応式

HRID 1177891 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH2:16][C:15]([F:20])([C:17]([OH:19])=O)[CH:14]=[CH:13][C:12]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:49][CH2:50][C:51]([N:53]1[CH2:58][CH2:57][N:56]([C:59](=[O:70])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])[CH2:55][CH2:54]1)=[O:52]>CN(C=O)C.C(OCC)(=O)C.O>[O:52]=[C:51]([N:53]1[CH2:54][CH2:55][N:56]([C:59](=[O:70])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])[CH2:57][CH2:58]1)[CH2:50][NH:49][C:17]([C:15]1([F:20])[CH:14]=[CH:13][C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]([F:10])[CH2:16]1)=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochlorideHCID 669533272,4-Difluoro-biphenyl-4-carboxylic acid

生成物 1

HCID 86634089
2,4-Difluoro-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
収率 50.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

DIPEA (83 mg, 0.11 mL, 0.21 mmol) was added to a stirred solution of 2,4-difluoro-biphenyl-4-carboxylic acid (50 mg, 0.21 mmol) in DMF (1 mL). HOBT (35 mg, 0.25 mmol) and EDCI (50 mg, 0.25 mmol) were then added at room temperature. After 2 minutes 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (90 mg, 0.25 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and then extrated with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure to afford 56.9 mg (50.35%) of 2,4-difluoro-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 95.42%. 1H NMR (DMSO-d6): δ 8.2-7.94 (d, 2H), 7.88-7.74 (m, 2H), 7.74-7.6 (m, 4H), 7.6-7.5 (m, 1H), 7.46-7.34 (m, 1H), 7.3-7.2 (m, 1H), 4.3-4.1 (m, 2H), 3.8-3.4 (m, 6H), 3.2-3.0 (m, 2H).

後処理

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1e79d29a93a3425e95b53c9ba16e7ff2
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842696B2

反応ノート

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