1-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one → 1-(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)-2-piperidinone

HRID 1618700Notes

Reaction equation

HRID 1618700 reaction equation
Br[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][CH2:17][CH2:16][C:15]2=[O:20])[C:3]=1[CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]3[NH:36][CH2:35][C:34]4([CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[C:31]3=[N:32][CH:33]=2)[CH2:24][CH2:23]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:36]1[C:30]3[C:31](=[N:32][CH:33]=[C:28]([N:25]4[CH2:26][CH2:27][O:22][CH2:23][CH2:24]4)[CH:29]=3)[C:34]3([CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:35]1)=[C:3]([CH3:21])[C:4]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=[O:20])=[N:5]2

Participants

4

Reactant 2

HCID 596310611-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-oneHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 672845421-(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)-2-piperidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one (45.0 mg, 0.130 mmol) and 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] in toluene to give 1-(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)-2-piperidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.58 (1H, t, J=2.3 Hz), 7.55 (1H, d, J=9.4 Hz), 6.89-7.07 (1H, m), 5.55-6.01 (1H, m), 3.98-4.39 (4H, m), 3.46-3.93 (7H, m), 2.88-3.26 (4H, m), 2.54-2.72 (2H, m), 1.92-2.47 (8H, m), 1.61-1.90 (4H, m). Mass Spectrum (ESI) m/e=550.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c8bea63fc5d74bc2804991847e0d054d
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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