Hydrochloric Acid → HCID 67285457, compound

HRID 1618794Notes

Reaction equation

HRID 1618794 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH:26]=4)[C:21]4([CH2:38][O:37]C(C)(C)[O:35][CH2:34]4)[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[CH:26]=4)[C:21]([CH2:38][OH:37])([CH2:34][OH:35])[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67285789HCID 67285789, compound

Product 1

HCID 67285457HCID 67285457, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1′-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indoline] (0.057 g, 0.105 mmol) in THF (1 mL) was added 1.0 N HCl (1.05 mL, 1.05 mmol). After stirring at rt for 1 h, the solution was purified by column chromatography (eluting with a gradient of 0-10% MeOH in DCM) to give (1-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-6-morpholinoindoline-3,3-diyl)dimethanol as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.72 (1H, d, J=4.89 Hz), 8.03 (1H, td, J=7.70, 1.71 Hz), 7.97 (1H, dd, J=9.29, 6.11 Hz) 7.92 (1H, d, J=7.83 Hz), 7.84 (1H, dd, J=10.15, 2.57 Hz), 7.47-7.57 (2H, m), 7.06 (1H, d, J=8.07 Hz), 6.21 (1H, dd, J=8.19, 2.08 Hz), 5.45 (1H, d, J=1.96 Hz), 4.91 (1H, t, J=5.26 Hz), 4.84 (1H, t, J=5.26 Hz), 3.79-3.91 (2H, m), 3.72 (2H, d, J=5.38 Hz), 3.65 (2H, dd, J=5.38, 1.22 Hz), 3.58 (4H, t, J=4.89 Hz), 2.76-2.89 (4H, m), 2.29 (s, 3H). Mass Spectrum (ESI) m/e=501.2 (M+1).

Workup

  1. customthe solution was purified by column chromatography (
  2. washeluting with a gradient of 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-c1975476a45d468b915010e89518eaa3
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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