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

HRID 1860258Notes

Reaction equation

HRID 1860258 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.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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 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 (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].

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-86a2cfa146b54db29c16685945a7102b
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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