Potassium Carbonate → HCID 9907577, compound

HRID 1814418Notes

Reaction equation

[CH2:1](I)[CH2:2][CH3:3].[C:5]1([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:5]1([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[CH2:1][CH2:2][CH3:3])=[O:13])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Propyl iodide (51 mg, 0.30 mmol) was added to a mixture of N-phenylcarbamoyl-N′-[2-(4-chlorophenyl)ethyl]-1,3-diaminopropane (33 mg, 0.10 mmol) and potassium carbonate (28 mg, 0.20 mmol) in CH3CN (2 ml). The mixture was stirred at 75° C. for 5 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was purified by preparative normal phase HPLC using linear gradients of (A) chloroform and (B) methanol (0-5% B, in 0-10 min; 5-10% B, in 10-30 min; 10-15% B, in 30-40 min) at a flow rate of 10 ml/min. Fractions containing the major peak were pooled and concentrated to afford N-phenylcarbamoyl-N′-[2-(4-chlorophenyl)ethyl]-N′-propyl-1,3 diaminopropane (27 mg, 59%): MS(ES+) m/e 374 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=8.3 Hz, 2H), 7.25 (m, 4H), 7.07 (m, 3H), 5.98 (br, 1H), 5.00 (br, 1H), 3.31 (m, 2H), 2.78 (m, 6H), 2.59 (m, 2H), 1.76 (m, 2H), 1.52 (m, 2H), 0.90 (t, J=7.3 Hz, 3H).

Workup

filtrationfiltered
concentrationThe filtrate was concentrated under vacuum to dryness
customthe residue was purified by preparative normal phase
customgradients of (A) chloroform and (B) methanol (0-5% B, in 0-10 min; 5-10% B, in 10-30 min; 10-15% B, in 30-40 min)
additionFractions containing the major peak
concentrationconcentrated

Sources & evidence

ORD record: ord-dda26fc2d0c14f04a53891a0cbeb65f7
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875884B1

Reaction notes

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