5-Morpholinopyridin-3-amine → Tert-butyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate

HRID 1431626Notes

Reaction equation

HRID 1431626 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]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:3]=1[CH3:27].[O:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:35]=[C:36]([NH2:40])[CH:37]=[N:38][CH:39]=2)[CH2:30][CH2:29]1>C1(C)C=CC=CC=1>[F:12][C:10]1[CH:9]=[C:8]([F:13])[CH:7]=[C:6]2[C:11]=1[C:2]([NH:40][C:36]1[CH:37]=[N:38][CH:39]=[C:34]([N:31]3[CH2:32][CH2:33][O:28][CH2:29][CH2:30]3)[CH:35]=1)=[C:3]([CH3:27])[C:4]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]1)=[N:5]2

Participants

4

Reactant 2

HCID 583477375-Morpholinopyridin-3-amineHCID 59631055Tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate

Product 1

HCID 57449790Tert-butyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Essentially prepared according to Procedure H using tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate (85.0 mg, 0.210 mmol) and 5-morpholinopyridin-3-amine in toluene to give tert-butyl 4-(5,7-difluoro-3-methyl-4-(5-morpholinopyridin-3-ylamino)quinolin-2-yl)piperazine-1-carboxylate. 1H NMR (CDCl3) δ ppm 7.93 (1H, d, J=2.3 Hz), 7.70 (1H, d, J=2.2 Hz), 7.29 (1H, ddd, J=10.0, 2.5, 1.2 Hz), 6.90 (1H, d, J=12.9 Hz), 6.80 (1H, ddd, J=13.8, 8.8, 2.6 Hz), 6.57 (1H, t, J=2.3 Hz), 3.85 (4H, dd, J=5.6, 4.0 Hz), 3.52-3.63 (4H, m), 3.27-3.35 (4H, m), 3.10-3.17 (4H, m), 2.07 (3H, s), 1.50 (9H, s). Mass Spectrum (ESI) m/e=541.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-63e52e1b6dc14e6a9bd41fefa3058fb8
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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