1,2-Dichloroethane → HCID 67508605, compound

HRID 1431775Notes

Reaction equation

HRID 1431775 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]=[C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[CH:28]=3)[C:23](O)=[O:24])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.C(Cl)CCl.[CH2:39]([NH2:41])[CH3:40].C1COCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:39]([NH:41][C:23](=[O:24])[C:22]1[CH:26]=[C:27]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[CH:28]=[C:20]([NH:19][C:6]2[C:5]3[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:7]=2[CH3:18])[CH:21]=1)[CH3:40]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 59631079HCID 59631079, compoundHCID 66726184Ethylamine tetrahydrofuran

Product 1

HCID 67508605HCID 67508605, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to Procedure U by stirring 3-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-morpholinobenzoic acid (0.025 g, 0.055 mmol), DMAP (0.013 g, 0.109 mmol), EDC (0.021 g, 0.109 mmol), 2M ethanamine THF (0.035 mL, 0.071 mmol), and DCM (0.6 mL) at 23° C. for 1 hour. Purification by reverse-phase HPLC afforded N-ethyl-3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)benzamide as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67-8.71 (1H, m), 8.61 (1H, s), 8.27 (1H, m), 8.09 (1H, dd, J=9.3, 6.2 Hz), 7.97-8.02 (1H, m), 7.84-7.91 (1H, m), 7.71-7.77 (1H, m), 7.45-7.52 (2H, m), 6.86-6.89 (1H, m), 6.59-6.62 (1H, m), 6.44-6.48 (1H, m), 3.69-3.75 (4H, m), 3.17-3.25 (2H, m), 3.05-3.11 (4H, m), 2.16-2.20 (3H, m), 1.04-1.10 (3H, m). Mass Spectrum (ESI) m/e=486.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by reverse-phase HPLC

Sources & evidence

ORD record
ord-d62068181fe44aa1add9245beae21e83
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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