2,5-Dimorpholinopyridin-3-amine → Tert-butyl 4-(4-(2,5-dimorpholinopyridin-3-ylamino)-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate

HRID 1431651Notes

Reaction equation

HRID 1431651 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[C:39]([NH2:40])=[CH:38][C:37]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[CH:36][N:35]=2)[CH2:30][CH2:29]1>C1(C)C=CC=CC=1>[O:28]1[CH2:33][CH2:32][N:31]([C:34]2[C:39]([NH:40][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]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]4)[C:3]=3[CH3:27])=[CH:38][C:37]([N:41]3[CH2:42][CH2:43][O:44][CH2:45][CH2:46]3)=[CH:36][N:35]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 596310462,5-Dimorpholinopyridin-3-amineHCID 59631055Tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate

Product 1

HCID 59631461Tert-butyl 4-(4-(2,5-dimorpholinopyridin-3-ylamino)-5,7-difluoro-3-methylquinolin-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 (240.0 mg, 0.60 mmol) and 2,5-dimorpholinopyridin-3-amine in toluene to give tert-butyl 4-(4-(2,5-dimorpholinopyridin-3-ylamino)-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate. 1H NMR (CDCl3) δ ppm 7.62 (1H, d, J=2.7 Hz), 7.57 (1H, d, J=11.2 Hz), 7.31 (1H, d, J=7.6 Hz), 6.80 (1H, ddd, J=13.4, 8.8, 2.5 Hz), 6.25 (1H, d, J=2.5 Hz), 3.88-3.94 (4H, m), 3.72-3.83 (4H, m), 3.62 (4H, br. s.), 3.36 (4H, br. s.), 3.15 (4H, br. s.), 2.90-3.04 (4H, m), 2.11 (3H, s), 1.48-1.56 (9H, m). Mass Spectrum (ESI) m/e=626.3 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-0c54c2551c2944e1aebb181df57ac417
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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