O-Phenylenediamine → HCID 51039080, compound

HRID 2360087Notes

Reaction equation

HRID 2360087 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[C:20]([NH:22][CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)=[O:21])=[CH:5][CH:4]=1.[C:33]1([NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH2:39].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C>[NH2:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[NH:40][C:28]([C:27]1[CH:31]=[CH:32][C:24]([CH2:23][NH:22][C:20]([C:10]2[NH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:13][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[O:21])=[CH:25][CH:26]=1)=[O:30]

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67078571HCID 67078571, compound

Product 1

HCID 51039080HCID 51039080, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoic acid (0.213 g, 0.5 mmol) and phenylenediamine (0.108 g, 1.0 mmol) in DMF (10 ml) was cooled to 0° C. Triethylamine (0.40 ml, 2.87 mol), 1-hydroxybenzotriazole (0.101 g, 0.75 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.144 g, 0.75 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 (40 ml) was added, and the obtained solution was washed with water (7 ml), Na2S2O3 1N (7 ml, aqueous solution), water (7 ml), NaHCO3 (7 ml, saturated aqueous solution), and NaCl (7 ml, saturated aqueous solution), dried over Na2SO4 and evaporated under reduced pressure, to obtain 0.142 g (0.27 mmol) of N-(4-{[(2-aminophenyl)amino]carbonyl}benzyl)-3-(4-methoxyphenyl)-5-Phenyl-1H-pyrrole-2-carboxamide: Yield 55%; m.p. 142-143° C. (dec); IR 3407, 3296, 1627, 1530, 1493, 1246 cm−1; 1H-NMR (300 MHz, δ ppm, DMSO-d6) 11.54 (s, 1H), 9.61 (s, 1H), 7.95 (d, J=7.8 Hz, 3H), 7.80 (d, J=7.4 Hz, 2H), 7.45-7.38 (m, 6H), 7.26 (t, J=7.3 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 6.97 (dt, J=8.0 Hz, J′=1.4 Hz, 1H), 6.90 (d, J=8.7 Hz, 2H), 6.79 (dd, J=7.9 Hz, J′=1.1 Hz, 1H), 6.67 (d, J=2.6 Hz, 1H), 6.60 (dt, J=7.5 Hz, J′=1.0 Hz, 1H), 4.86 (s, 2H), 4.49 (d, J=5.7 Hz, 2H), 3.77 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 165.0, 161.1, 157.9, 143.0, 142.9, 133.1, 132.9, 131.5, 129.9, 128.6, 127.9, 127.8, 127.7, 127.1, 126.7, 126.6, 126.4, 124.5, 123.3, 122.6, 116.2, 116.1, 113.4, 108.3, 55.0, 42.1.

Workup

  1. waitfor an additional 96 h at room temperature
  2. washthe obtained solution was washed with water (7 ml), Na2S2O3 1N (7 ml, aqueous solution), water (7 ml), NaHCO3 (7 ml, saturated aqueous solution), and NaCl (7 ml, saturated aqueous solution)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f4c52d23e7994e2fb2e886b2a88a35b9
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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