Tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate → US8765940, tert-butyl 4-(5,7-difluoro-3-methyl-4-(6'-(4-morpholinyl)-2,3,5,6-tetrahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridin]-1'(2'H)-yl)-2-quinolinyl)-1-piperazinecarboxylate

HRID 1618751Notes

Reaction equation

HRID 1618751 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]3[NH:42][CH2:41][C:40]4([CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[C:37]3=[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]([N:42]1[C:36]3[C:37](=[N:38][CH:39]=[C:34]([N:31]4[CH2:32][CH2:33][O:28][CH2:29][CH2:30]4)[CH:35]=3)[C:40]3([CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[CH2:41]1)=[C:3]([CH3:27])[C:4]([N:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:18][CH2:19]1)=[N:5]2

Participants

4

Reactant 2

HCID 59631055Tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylateHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 67285378US8765940, tert-butyl 4-(5,7-difluoro-3-methyl-4-(6'-(4-morpholinyl)-2,3,5,6-tetrahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridin]-1'(2'H)-yl)-2-quinolinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using tert-butyl 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)piperazine-1-carboxylate (690.0 mg, 1.70 mmol) and 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] in toluene to give tert-butyl 4-(5,7-difluoro-3-methyl-4-(6′-(4-morpholinyl)-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-1′(2′H)-yl)-2-quinolinyl)-1-piperazinecarboxylate. 1H NMR (400 MHz, chloroform-d) δ ppm 7.56 (1H, d, J=2.3 Hz), 7.35 (1H, ddd, J=9.8, 2.4, 1.1 Hz), 6.75 (1H, ddd, J=11.8, 8.9, 2.5 Hz), 5.66 (1H, d, J=2.3 Hz), 4.05-4.22 (2H, m), 3.80-3.98 (2H, m), 3.71-3.79 (4H, m), 3.48-3.71 (6H, m), 3.24-3.44 (4H, m), 2.89-3.06 (4H, m), 2.26-2.43 (2H, m), 2.25 (3H, s), 1.64-1.87 (3H, m), 1.51 (9H, s). Mass Spectrum (ESI) m/e=637.5 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-270dd56ff1e7487099357af933be0f7b
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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