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 1860265Notes

Reaction equation

HRID 1860265 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-bb8c46aa1c4543f9b3ae3bf0e33e9971
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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