N,N-Diethyl-p-phenylenediamine → HCID 59314055, compound

HRID 889468Notes

Reaction equation

HRID 889468 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:13]([CH:23]2[CH2:25][CH2:24]2)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[CH2:26]([N:28]([CH2:36][CH3:37])[C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1)[CH3:27].CN1C(=O)CCC1>CO>[CH:23]1([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:4]2[C:5]3[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=3)[N:7]=[C:2]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([N:28]([CH2:36][CH3:37])[CH2:26][CH3:27])=[CH:34][CH:33]=3)[CH:3]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 13387N-methyl-2-pyrrolidoneHCID 593137576-Chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile

Product 1

HCID 59314055HCID 59314055, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A microwave tube was charged with 1G (30 mg, 0.085 mmol), N1,N1-diethylbenzene-1,4-diamine (139 mg, 0.85 mmol), and NMP (1 mL). The mixture was irradiated in a microwave for three cycles of 15 min. (300W), 120° C. The crude reaction mixture was dissolved in a small amount of MeOH and purified by reversed phase HPLC (YMC ODS-A 5 um 30×250 mm, 10-90% aqueous methanol containing 0.1% TFA, 25 mL/min., 30 min. gradient, monitored at 220 nm) to afford 244A, (5 mg, 9.0% yield). HPLC: Rt=3.896 min. (YMC S5 ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min. gradient, monitored at 220 nm). MS (ES): m/z=482.1 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. custompurified by reversed phase HPLC (YMC ODS-A 5 um 30×250 mm, 10-90% aqueous methanol containing 0.1% TFA, 25 mL/min., 30 min. gradient, monitored at 220 nm)

Sources & evidence

ORD record
ord-369212dbf28d415a967e5f620edbdb74
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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