HCID 59631406, compound → HCID 67284766, compound

HRID 1618774Notes

Reaction equation

HRID 1618774 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[CH2:17][CH2:16][C:15]2=[O:18])[C:3]=1[CH3:19].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]3[NH:34][CH2:33][C:32]4([CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[C:29]3=[N:30][CH:31]=2)[CH2:22][CH2:21]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:34]1[C:28]3[C:29](=[N:30][CH:31]=[C:26]([N:23]4[CH2:24][CH2:25][O:20][CH2:21][CH2:22]4)[CH:27]=3)[C:32]3([CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH2:33]1)=[C:3]([CH3:19])[C:4]([N:14]1[CH2:17][CH2:16][C:15]1=[O:18])=[N:5]2

Participants

4

Reactant 2

HCID 59631406HCID 59631406, compoundHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 67284766HCID 67284766, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)azetidin-2-one (130 mg, 0.44 mmol) and 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] in toluene (except using cesium carbonate as base) 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-azetidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.59 (1H, d, J=2.3 Hz), 7.45 (1H, ddd, J=9.5, 2.4, 1.2 Hz), 6.89 (1H, ddd, J=11.8, 9.0, 2.4 Hz), 5.72 (1H, d, J=2.3 Hz), 4.13 (2H, m, J=11.6, 4.2, 4.0, 4.0 Hz), 4.00-4.09 (2H, m), 3.98 (1H, d, J=9.4 Hz), 3.85 (1H, d, J=9.4 Hz), 3.69-3.80 (4H, m), 3.57 (2H, m, J=11.7, 11.7, 2.9, 2.7 Hz), 3.16 (2H, t, J=5.0 Hz), 2.96-3.07 (4H, m), 2.39 (3H, s), 2.31 (2H, dddd, J=15.8, 8.9, 8.6, 4.5 Hz), 1.80 (1H, d, J=14.5 Hz), 1.67-1.75 (1H, m). Mass Spectrum (ESI) m/e=522.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-bb40a3b5a4424401b10e08437e3c577b
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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