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

HRID 1431649Notes

Reaction equation

HRID 1431649 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]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH: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>[F:13][C:8]1[CH:9]=[C:10]([F:12])[CH:11]=[C:6]2[C:7]=1[C:2]([NH:39][C:35]1[CH:36]=[N:37][CH:38]=[C:33]([N:30]3[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)[CH:34]=1)=[C:3]([CH3:26])[C:4]([N:14]1[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]1)=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 596314674-Chloro-5,7-difluoro-3-methyl-2-(4-phenylpiperazin-1-yl)quinoline

Product 1

HCID 596310785,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(4-phenylpiperazin-1-yl)quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using 4-chloro-5,7-difluoro-3-methyl-2-(4-phenylpiperazin-1-yl)quinoline (40.0 mg, 0.11 mmol) and 5-morpholinopyridin-3-amine in toluene to give 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(4-phenylpiperazin-1-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 7.94 (1H, d, J=2.5 Hz), 7.72 (1H, d, J=2.2 Hz), 7.28-7.36 (3H, m), 7.01 (2H, dd, J=8.8, 1.0 Hz), 6.87-6.96 (2H, m), 6.81 (1H, ddd, J=13.8, 8.8, 2.6 Hz), 6.61 (1H, t, J=2.3 Hz), 3.81-3.88 (4H, m), 3.48-3.57 (4H, m), 3.29-3.45 (4H, m), 3.18 (4H, dd, J=5.8, 4.0 Hz), 2.12 (3H, s). Mass Spectrum (ESI) m/e=517.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-02f38cc5c4d448f595893540926e6819
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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