Hydrochloric Acid → 1-(7-Fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

HRID 1618504Notes

Reaction equation

HRID 1618504 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:3]=1[CH3:19].[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[C:30]3[NH:32][CH2:33][C:34]4([CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[C:29]3=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.Cl.O1CCOCC1>>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:32]3[C:30]4[C:29](=[CH:28][CH:27]=[C:26]([N:23]5[CH2:22][CH2:21][O:20][CH2:25][CH2:24]5)[CH:31]=4)[C:34]4([CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[CH2:33]3)=[C:3]([CH3:19])[C:4]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596310524-Chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinolineHCID 672846616-Morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

Product 1

HCID 672846361-(7-Fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]

Procedure

Prepare according to procedure L using 4-chloro-7-fluoro-3-methyl-2-(pyridin-3-yl)quinoline (75 mg, 0.27 μmol), 6-morpholino-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (75 mg, 0.27 mmol) and a 4.0M solution of HCl in 1,4-dioxane (0.014 mL, 0.055 mmol). After purification 1-(7-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.91 (1H, d, J=2.3 Hz), 8.73 (1H, dd, J=4.9, 1.8 Hz), 8.01 (1H, dt, J=7.8, 2.2 Hz), 7.76-7.89 (2H, m), 7.48 (1H, dd, J=8.0, 4.9 Hz), 7.27 (1H, dd, J=17.6, 2.7 Hz), 7.14 (1H, d, J=8.2 Hz), 6.36 (1H, dd, J=8.2, 2.3 Hz), 5.61 (1H, d, J=2.3 Hz), 4.00-4.09 (2H, m), 3.91-3.99 (2H, m), 3.70-3.79 (4H, m), 3.50-3.61 (2H, m, J=12.0, 12.0, 2.5, 2.3 Hz), 2.90-3.02 (4H, m), 2.30 (3H, s), 2.10-2.24 (2H, m), 1.89 (1H, dd, J=13.7, 2.3 Hz), 1.75-1.82 (1H, m). Mass Spectrum (ESI) m/e=511 (M+1).

Workup

  1. customPrepare
  2. customAfter purification 1-(7-fluoro-3-methyl-2-(3-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran]
  3. customwas obtained as a yellow film

Sources & evidence

ORD record
ord-9831e33bfb9f49a48d675ff97a9650af
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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