Toluene → HCID 59631495, compound

HRID 1431611Notes

Reaction equation

HRID 1431611 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH3:21])[C:16](=[O:22])[CH2:15]2)[C:3]=1[CH3:23].[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([NH2:36])=[CH:34][C:33]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1.[C:43]1(C)C=CC=CC=1>>[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([NH:36][C:2]3[C:11]4[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=4[F:12])[N:5]=[C:4]([N:14]4[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH3:43])[C:16](=[O:22])[CH2:15]4)[C:3]=3[CH3:23])=[CH:34][C:33]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:32][N:31]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 596310462,5-Dimorpholinopyridin-3-amineHCID 59631366HCID 59631366, compound

Product 1

HCID 59631495HCID 59631495, compound

Procedure

Essentially prepared according to Procedure H using 4-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)-1-ethylpiperazin-2-one (35.0 mg, 0.088 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give 4-(4-(2,5-dimorpholinopyridin-3-ylamino)-5,7-difluoro-3-methylquinolin-2-yl)-1-propylpiperazin-2-one. 1H NMR (TFA salt) (400 MHz, CDCl3) δ ppm 7.79 (1H, d, J=2.5 Hz), 7.72 (1H, d, J=10.8 Hz), 7.40 (1H, ddd, J=9.7, 2.4, 1.2 Hz), 6.88 (1H, ddd, J=13.5, 8.6, 2.5 Hz), 6.47 (1H, d, J=2.7 Hz), 5.94 (3H, br. s.), 3.96-4.35 (3H, m), 3.87-3.95 (4H, m), 3.77-3.86 (4H, m), 3.54-3.76 (2H, m), 3.12-3.54 (7H, m), 2.99-3.13 (4H, m), 2.14 (3H, s), 1.63 (2H, sxt, J=7.5 Hz), 0.93 (3H, t, J=7.4 Hz). Mass Spectrum (ESI) m/e=582.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-2c3d211f93764eee8ae98feae1fc5cc0
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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