1-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-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-pyrrolidinone

HRID 1618710Notes

Reaction equation

HRID 1618710 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[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[C:3]=1[CH3:20].[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:28]=[C:29]3[NH:35][CH2:34][C:33]4([CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[C:30]3=[N:31][CH:32]=2)[CH2:23][CH2:22]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:35]1[C:29]3[C:30](=[N:31][CH:32]=[C:27]([N:24]4[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)[CH:28]=3)[C:33]3([CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:34]1)=[C:3]([CH3:20])[C:4]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])=[N:5]2

Participants

4

Reactant 2

HCID 596310731-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-oneHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 672856661-(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-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one (60.0 mg, 0.180 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-pyrrolidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.61 (1H, d, J=2.3 Hz), 7.49 (1H, ddd, J=9.4, 2.5, 1.4 Hz), 6.95 (1H, ddd, J=11.8, 8.9, 2.5 Hz), 5.86 (1H, d, J=2.2 Hz), 4.19-4.31 (1H, m), 4.02-4.19 (4H, m), 3.84 (1H, d, J=9.2 Hz), 3.70-3.78 (4H, m), 3.56 (2H, qd, J=11.5, 2.5 Hz), 2.94-3.12 (4H, m), 2.64 (2H, t, J=8.0 Hz), 2.24-2.40 (4H, m), 2.17 (3H, s), 1.82 (1H, d, J=13.5 Hz), 1.69 (1H, dd, J=13.9, 2.2 Hz). Mass Spectrum (ESI) m/e=536.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-124e9b5cf9ee4323a38905bf3f019a87
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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