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1-Hydroxybenzotriazole → 4-(5-cyano-pyridin-2-yloxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 1177981
ノート
印刷プレビュー

反応式

HRID 1177981 の反応式
CCN(C(C)C)C(C)C.OC(C(F)(F)F)=O.[NH2:17][CH2:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27](=[O:38])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:37])([F:36])[F:35])[CH2:23][CH2:22]1)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:61]([C:63]1[CH:64]=[CH:65][C:66]([O:69][C:70]2[CH:78]=[CH:77][C:73]([C:74](O)=[O:75])=[CH:72][CH:71]=2)=[N:67][CH:68]=1)#[N:62]>CN(C=O)C.O>[C:61]([C:63]1[CH:64]=[CH:65][C:66]([O:69][C:70]2[CH:78]=[CH:77][C:73]([C:74]([NH:17][CH2:18][C:19](=[O:20])[N:21]3[CH2:22][CH2:23][N:24]([C:27](=[O:38])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:35])[F:36])[CH2:25][CH2:26]3)=[O:75])=[CH:72][CH:71]=2)=[N:67][CH:68]=1)#[N:62]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 521758604-((5-Cyano-2-pyridinyl)oxy)benzoic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

生成物 1

HCID 25165126
4-(5-cyano-pyridin-2-yloxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide
収率 57.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (43 mg, 0.34 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt. (58 mg, 0.13 mmol) in DMF (1 mL). HOBT (18 mg, 0.13 mmol) and EDCI.HCl (26 mg, 0.13 mmol) were then added at room temperature. After 2 minutes, 4-(5-cyano-pyridin-2-yloxy)benzoic acid (30 mg, 0.11 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 34.4 mg (57.3% yield) of 4-(5-cyano-pyridin-2-yloxy)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 85.6%, 1H NMR (CDCl3): δ 8.5 (ds, 1H), 8.0-7.9 (s, 3H), 7.8-7.5 (m, 4H), 7.5-7.4 (m, 1H), 7.0 (m, 2H), 4.5-3.5 (m, 8H), 3.5-3.0 (m, 3H).

後処理

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3c009e93053d46919db43ec23d8d4816
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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