Water → HCID 86659149, compound

HRID 73258Notes

Reaction equation

HRID 73258 reaction equation
Cl.C(N=[C:5]=[N:6][CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])C.C([N:15]([CH2:18]C)CC)C.[CH:20]([C:22]1[NH:26][C:25]([CH3:27])=[C:24]([C:28]([OH:30])=O)[C:23]=1[CH3:31])=[O:21].ON1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2N=N1.[OH2:42]>CN(C=O)C>[CH2:12]([N:10]1[CH2:9][CH2:8][CH:7]([NH:6][C:5](=[O:42])[CH2:18][NH:15][C:28]([C:24]2[C:23]([CH3:31])=[C:22]([CH:20]=[O:21])[NH:26][C:25]=2[CH3:27])=[O:30])[CH2:11]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Product 1

HCID 86659149HCID 86659149, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.074 g, 5.6 mmol), triethylamine (1.12 mL, 8 mmol), 5-formyl-2,4-dimethyl-1H-pyrrole-3-formic acid (0.668 g, 4 mmol) and 1-hydroxybenzotriazole (0.756 g, 5.6 mmol) were sequentially added to DMF (10 mL) with stirring at about 0° C. and stirred for 1.5 hrs, and the compound obtained in the above step (1.86 g, 8 mmol) was added. The reaction was stirred at room temperature until completion was indicated by thin layer chromatography (TLC). 1.2 mL of water and 1 mL of saturated salt water were added, and the mixture was extracted with 10% methanol/dichloromethane (25 mL×3), the combined organic phase was washed with saturated salt water (25 mL×3), dried over anhydrous Na2SO4, and the solvent was distilled off under reduced pressure. The residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2) to give 0.614 g (1.61 mmol) of N-{2-[(1-benzylpyrrolidin-3-yl)amino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 40.2%. 1HNMR (DMSO-d6) δ10.81 (s, br, 1H, NH), 9.64 (s, 1H), 7.63 (m, br, 1H, CONHCH2), 6.92 (t, br, 1H, NH), 6.83-6.86 (m, 5H, benzene ring hydrogen), 3.81-3.75 (d, 2H), 3.67-3.68 (m, 1H), 3.50-3.669 (m, 2H), 3.16-3.17 (m, 2H), 2.32 (s, 3H), 2.33 (s, 3H), 1.71-1.82 (m, 2H), 1.10-1.11 (m, 2H).

Workup

  1. stirringstirred for 1.5 hrs
  2. customthe compound obtained in the above step (1.86 g, 8 mmol)
  3. additionwas added
  4. stirringThe reaction was stirred at room temperature until completion
  5. extractionthe mixture was extracted with 10% methanol/dichloromethane (25 mL×3)
  6. washthe combined organic phase was washed with saturated salt water (25 mL×3)
  7. dry with materialdried over anhydrous Na2SO4
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-c39f3ba142034a84812bc793cb4ce81a
Source dataset
uspto-grants-2014_09
Patent number
US08829039B2

Reaction notes

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