4-Methylmorpholine → HCID 67078970, compound

HRID 2360081Notes

Reaction equation

HRID 2360081 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[NH:10][C:9]([C:11]([OH:13])=O)=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:7]=2)=[CH:2]1.Cl.[NH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[NH:10][C:9]([C:11]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)=[O:13])=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:7]=2)=[CH:2]1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 67078538HCID 67078538, compound

Product 1

HCID 67078970HCID 67078970, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(3-furyl)-3-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylic acid (1.45 g, 5.5 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (1.10 g, 5.5 mmol) in DMF (27.5 ml) was cooled to 0° C. Triethylamine (4.22 ml, 30.25 mol), 1-hydroxybenzotriazole (0.81 g, 6.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.17 g, 6.0 mmol) and N-methylmorpholine (0.61 ml, 5.5 mmol) were added subsequently, and the mixture was stirred for 2 h at 0° C., and for an additional 96 h at room temperature. Ethyl acetate (400 ml) was added, and the obtained solution was washed with water (75 ml), Na2S2O3 1N (75 ml, aqueous solution), water (75 ml), NaHCO3 (75 ml, saturated aqueous solution), and NaCl (75 ml, saturated aqueous solution), dried over Na2SO4 and evaporated under reduced pressure, to obtain 1.43 g (3.47 mmol) of methyl 4-[({[5-(3-furyl)-3-(4-hydroxyphenyl)-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoate: Yield 63%; m.p. 223-224° C.; IR 3390, 3321, 1700, 1616, 1532, 1272 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 11.51 (s, 1H), 9.35 (s, 1H), 8.13 (s, 1H), 7.91 (d, J=8.2 Hz, 2H), 7.67 (tb, 1H), 7.37 (d, J=8.3 Hz, 3H), 7.26 (d, J=8.5 Hz, 2H), 6.93 (d, J=0.9 Hz, 1H), 6.73 (d, J=8.5 Hz, 2H), 6.38 (d, J=2.6 Hz, 1H), 4.45 (d, J=5.8 Hz, 2H), 3.85 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 166.0, 161.2, 156.3, 145.0, 143.6, 138.5, 129.9, 129.1, 128.1, 127.5, 127.4, 126.0, 125.9, 121.3, 118.2, 115.1, 108.7, 108.3, 51.9, 42.1.

Workup

  1. waitfor an additional 96 h at room temperature
  2. washthe obtained solution was washed with water (75 ml), Na2S2O3 1N (75 ml, aqueous solution), water (75 ml), NaHCO3 (75 ml, saturated aqueous solution), and NaCl (75 ml, saturated aqueous solution)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b1cd9a98cd554b819dd6a6f138422c0d
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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