Hydrochloric Acid → HCID 178467110, compound

HRID 2271844Notes

Reaction equation

HRID 2271844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:26][CH2:25]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].[ClH:34]>CO>[ClH:1].[ClH:34].[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:22])[CH3:21])=[C:13]3[NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([CH2:30][N:31]([CH3:32])[CH3:33])[CH2:26][CH2:25]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178467109HCID 178467109, compound

Product 1

HCID 178467110HCID 178467110, compoundYield 175.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-(6-(3-chloro-5-fluoro-4-hydroxyphenyl)-4-((trans-4-((dimethylamino)methyl)cyclohexyl)amino)quinolin-3-yl)ethanone (3.06 g, 6.51 mmol) in methanol (250 mL) was added HCl (1.25 M in MeOH, 25 mL, 31.2 mmol). The resultant suspension was partially concentrated, filtered and rinsed with ethyl acetate to give the desired product (3.10 g, 88%) as a light yellow solid. 1H NMR (500 MHz, MeOD) δ 9.00 (s, 1H), 8.38 (d, J=2.0 Hz, 1H), 8.10 (dd, J=8.7, 2.0 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.54 (dd, J=2.2, 1.5 Hz, 1H), 7.46 (dd, J=11.5, 2.3 Hz, 1H), 4.38-4.29 (m, 1H), 3.06 (d, J=6.6 Hz, 2H), 2.91 (s, 6H), 2.71 (s, 3H), 2.40 (d, J=12.7 Hz, 2H), 2.04-1.95 (m, 3H), 1.75-1.65 (m, 2H), 1.31 (q, J=12.8 Hz, 2H). ESI MS m/z 470 [C26H29ClFN3O2+H]+; HPLC>99% (AUC), tR=9.75 min.

Workup

  1. concentrationThe resultant suspension was partially concentrated
  2. filtrationfiltered
  3. washrinsed with ethyl acetate

Sources & evidence

ORD record
ord-c8f63f37e204462fa56676a3f34605e0
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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