Propylamine → (Z)-5,6-dihydro-5-oxo-N-propyl-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxamide

HRID 1860258ノート

反応式

HRID 1860258 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.O[N:20]1[C:24]2C=CC=[CH:28][C:23]=2N=N1.C(N)CC.Cl.CON(OC)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([NH:20][CH2:24][CH2:23][CH3:28])=[O:12])=[CH:9][C:4]=2/[C:3]/1=[CH:13]/[C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1

参加物

8

反応物 5

HCID 7852PropylamineHCID 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 18626972(Z)-5,6-dihydro-5-oxo-N-propyl-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxamide収率 38.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒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 (30 mg, 0.12 mmol), 1-hydroxy-benzotriazole (18 mg, 0.13 mmol), propylamine (11 μl, 0.13 mmol), 1-(3-dimethoxyaminopropyl)-3-ethylcarbodiimide hydrochloride (25 mg, 0.13 mmol) and diisopropylethylamine (23 μl, 0.13 mmol) in dimethylformamide (1 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 14 mg of (Z)-5,6-dihydro-5-oxo-N-propyl-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxamide as an orange solid. MS(ES): m/e 302 [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-86a2cfa146b54db29c16685945a7102b
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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