1,2-Dichloroethane → HCID 59631415, compound

HRID 1431776Notes

Reaction equation

HRID 1431776 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.[NH3:39].O1CCOCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[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]([NH2:39])=[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

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 59631079HCID 59631079, compound

Product 1

HCID 59631415HCID 59631415, 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 (0.014 g, 0.031 mmol), DMAP (7.46 mg, 0.061 mmol), EDC (0.023 g, 0.122 mmol), 0.5M ammonia in dioxane (0.092 mL, 0.046 mmol), and DCM (0.3 mL) at 23° C. for 48 h. Reverse-phase HPLC afforded 3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)benzamide as a yellow amorphous solid. 1H NMR (400 MHz, Methanol) δ ppm 8.72 (1H, br. s.), 7.98-8.27 (2H, m), 7.82 (1H, d, J=7.2 Hz), 7.67 (1H, d, J=9.6 Hz), 7.59 (1H, d, J=3.9 Hz), 7.39 (1H, m), 7.08 (1H, br. s.), 6.77 (1H, br. s.), 6.66 (1H, br. s.), 3.70-3.94 (4H, m), 3.03-3.25 (5H, m), 2.01-2.24 (3H, m). Mass Spectrum (ESI) m/e=457.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-90327176e61d4afea748db7eed62487d
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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