Hydrochloric Acid → HCID 178467083, compound

HRID 2271970Notes

Reaction equation

HRID 2271970 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]([Cl:9])[C:7]=1[OH:8].Cl.O>CO>[ClH:1].[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]([Cl:9])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178467082HCID 178467082, compound

Product 1

HCID 178467083HCID 178467083, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-{6-(3,5-dichloro-4-hydroxyphenyl)-4-[trans-4-((dimethylamino)methyl)cyclohexylamino]quinolin-3-yl}ethanone (200 mg, 0.410 mmol) in methanol (20 mL) was added 1M HCl in water (1.03 mL, 1.03 mmol). The resultant solution was concentrated to an approximate volume of 5 mL. The precipitate was washed with acetonitrile to obtain the desired product as the hydrochloride salt (200 mg) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.05 (s, 1H), 8.43 (d, J=1.9 Hz, 1H), 8.18 (dd, J=8.7, 1.9 Hz, 1H), 7.96 (d, J=8.7 Hz, 1H), 7.70 (s, 2H), 4.46-4.38 (m, 1H), 3.07 (d, J=6.6 Hz, 2H), 2.92 (s, 6H), 2.73 (s, 3H), 2.44 (d, J=12.2 Hz, 2H), 2.08-1.98 (m, 3H), 1.82-1.70 (m, 2H), 1.40-1.28 (m, 2H); ESI MS m/z 486 [C26H29Cl2N3O2+H]+; HPLC>99% (AUC), tR=9.94 min.

Workup

  1. concentrationThe resultant solution was concentrated to an approximate volume of 5 mL
  2. washThe precipitate was washed with acetonitrile

Sources & evidence

ORD record
ord-74ab2fa231874ab29ff0dc4a027952a2
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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