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

HRID 1860258노트

반응식

HRID 1860258 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-86a2cfa146b54db29c16685945a7102b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528653B2

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