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Triethylamine → thiophene-3-carboxylic acid N'-[2-(5-fluoro-2'-ethyl-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazide

HRID 2250935
ノート
印刷プレビュー

反応式

HRID 2250935 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:17][C:18]([OH:20])=O)[CH3:2].[CH:21]([NH:24][NH:25][C:26]([C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)=[O:27])([CH3:23])[CH3:22].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[F:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH2:17][C:18]([N:24]([CH:21]([CH3:23])[CH3:22])[NH:25][C:26]([C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[O:27])=[O:20])=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:1][CH3:2])[CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 58689898(2'-Ethyl-5-fluoro-biphenyl-2-yloxy)-acetic acidHCID 59642162thiophene-3-carboxylic acid N'-isopropyl-hydrazide

生成物 1

HCID 11597369
thiophene-3-carboxylic acid N'-[2-(5-fluoro-2'-ethyl-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazide
収率 73.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (2′-ethyl-5-fluoro-biphenyl-2-yloxy)-acetic acid (100 mg, 0.36 mmol), and tiophene-3-carboxylic acid-N′-isopropyl hydrazide (32 mg, 0.1268 mmol) in DMF (5 mL), was treated with triethylamine (0.152 ml, 1.09 mmol), HOBT (59 mg, 0.44 mmol), and EDCI (84 mg, 0.44 mmol) for 12 hours at room temperature. The reaction mixture was partitioned between 1N HCl and DCM. The organic layer was successively washed with 1N NaOH and brine, then dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as a solid (41 mg, 26%). MS m/e 441.30 (M+H+)

後処理

  1. customThe reaction mixture was partitioned between 1N HCl and DCM
  2. washThe organic layer was successively washed with 1N NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-e8d5ac58243b49ea9fb0245f6946bc73
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07317125B2

反応ノート

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