5-Morpholinopyridin-3-amine → 2-(4-cyclohexylpiperazin-1-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

HRID 1431647Notes

Reaction equation

HRID 1431647 reaction equation
Cl[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]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:16][CH2:15]2)[C:3]=1[CH3:26].[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:34]=[C:35]([NH2:39])[CH:36]=[N:37][CH:38]=2)[CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[CH:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:4]3[C:3]([CH3:26])=[C:2]([NH:39][C:35]4[CH:36]=[N:37][CH:38]=[C:33]([N:30]5[CH2:31][CH2:32][O:27][CH2:28][CH2:29]5)[CH:34]=4)[C:11]4[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=4[F:12])[N:5]=3)[CH2:15][CH2:16]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596312584-Chloro-2-(4-cyclohexylpiperazin-1-yl)-5,7-difluoro-3-methylquinoline

Product 1

HCID 596310472-(4-cyclohexylpiperazin-1-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 4-chloro-2-(4-cyclohexylpiperazin-1-yl)-5,7-difluoro-3-methylquinoline (22.0 mg, 0.058 mmol) and 5-morpholinopyridin-3-amine in toluene to give 2-(4-cyclohexylpiperazin-1-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 7.93 (1H, d, J=2.3 Hz), 7.70 (1H, d, J=1.8 Hz), 7.27-7.33 (1H, m), 6.86 (1H, d, J=12.9 Hz), 6.78 (1H, ddd, J=13.9, 8.6, 2.5 Hz), 6.57 (1H, t, J=2.3 Hz), 3.79-3.91 (4H, m), 3.35-3.61 (4H, m), 3.07-3.23 (4H, m), 2.70-2.98 (4H, m), 2.06 (3H, s), 1.91-2.03 (2H, m), 1.77-1.91 (2H, m), 1.67 (1H, d, J=12.9 Hz), 1.05-1.41 (6H, m). Mass Spectrum (ESI) m/e=524.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-50a22f3b322c48a799e3767c013f5467
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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