Dimethylformamide → (Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno [2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide

HRID 1860265ノート

反応式

HRID 1860265 の反応式
[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2/[C:3]/1=[CH:13]/[C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1.ON1C2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.Cl.C[O:31][N:32](OC)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.CN(C)C=[O:55]>C(OCC)(=O)C>[O:55]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:31][NH:32][C:10]([C:8]1[S:7][C:5]2[NH:6][C:2](=[O:1])/[C:3](=[CH:13]\[C:14]3[NH:15][CH:16]=[CH:17][CH:18]=3)/[C:4]=2[CH:9]=1)=[O:12]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 219844591-(3-Dimethoxyaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 69844590(Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acid

生成物 1

HCID 86584528(Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno [2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acid (250 mg, 0.95 mmol), 1-hydroxybenzotriazole (1.1 mmol, 150 mg), 1-(tetrahydro-pyran-2-yloxy) amine (1.25 mmol, 146 mg), 1-(3-dimethoxyaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 mmol, 208 mg) and diisopropylethylamine (1.1 mmol, 190 mg) in dimethylformamide (4 ml) was stirred at room temperature for 3 hours then diluted with ethyl acetate and washed with 2M hydrochloric acid, saturated sodium bicarbonate and water. The resulting solution was dried over magnesium sulfate and evaporated to dryness. The residue was triturated with water/isopropyl alcohol to give 90 mg of (Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno[2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide as a brown solid. MS(ES): m/e 360 [M+H].

後処理

  1. washwashed with 2M hydrochloric acid, saturated sodium bicarbonate and water
  2. dry with materialThe resulting solution was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customThe residue was triturated with water/isopropyl alcohol

出典と根拠

ORDレコード
ord-bb8c46aa1c4543f9b3ae3bf0e33e9971
出典データセット
uspto-grants-2003_03
特許番号
US06528653B2

反応ノート

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