4-Ethoxyaniline → HCID 59304458, compound

HRID 2239859Notes

Reaction equation

HRID 2239859 reaction equation
Cl.Cl.[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)=[CH:9][CH:8]=[N:7]2.CCOC1C=CC(N)=CC=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43](O)=[O:44])[C:38]2=[O:46])=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CC#N>[F:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:10]4[C:11]5[N:6]([CH:5]=[CH:4][N:3]=5)[N:7]=[CH:8][CH:9]=4)=[CH:14][CH:15]=3)=[O:44])[C:38]2=[O:46])=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 90764-EthoxyanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 131728136HCID 131728136, compound

Product 1

HCID 59304458HCID 59304458, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a 2 dram vial was added N1-(imidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamine di-HCl salt (0.080 g, 0.3 mmol) from 1c, 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (0.13 g, 0.57 mmol), EDCI (0.11 g, 0.57 mmol), HOBt (0.077 g, 0.57 mmol), TEA (0.16 ml, 1.1 mmol), and CH3CN (4 ml). The reaction was allowed to stir around 25° C. for 12 hrs. The solvent was then removed in vacuo and the sample was diluted with MeOH (4 ml). The solution was purified by HPLC (20-100% methanol gradient), which yielded 0.015 g of the title compound as a TFA salt. 1H NMR (400 MHz, DMSO-D6) δ ppm 11.96 (1H, s), 9.47 (1H, s), 8.59 (1H, dd, J=7.38, 2.29 Hz), 7.99-8.27 (3H, m), 7.67-7.85 (3H, m), 7.55-7.67 (2H, m, J=9.16, 5.09 Hz), 7.33-7.49 (3H, m), 6.66-6.82 (1H, m), 6.55 (1H, d, J=6.10 Hz) LC/MS, m/e 441 (M+1). HPLC Rt, 2.64 min. YMC ODSC18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. customThe solvent was then removed in vacuo
  2. additionthe sample was diluted with MeOH (4 ml)
  3. customThe solution was purified by HPLC (20-100% methanol gradient), which

Sources & evidence

ORD record
ord-09570f09c9dc4c148dec93d249bea21e
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

Loading…