Hydrochloric Acid → {6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone dihydrochloride

HRID 2271737Notes

Reaction equation

HRID 2271737 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([CH:23]2[CH2:25][CH2:24]2)=[O:22])=[C:14]3[NH:26][CH:27]2[CH2:32][CH2:31][CH:30]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH2:29][CH2:28]2)[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[ClH:38]>>[ClH:1].[ClH:38].[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([CH:23]2[CH2:24][CH2:25]2)=[O:22])=[C:14]3[NH:26][CH:27]2[CH2:32][CH2:31][CH:30]([N:33]([CH2:34][CH3:35])[CH2:36][CH3:37])[CH2:29][CH2:28]2)[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66716203{6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone

Product 1

HCID 86692924{6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone dihydrochlorideYield 75%

Procedure

To {6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (18 mg, 0.34 mmol) was added 1 M HCl (5 mL) and the mixture was concentrated to afford the desired product (15 mg, 75%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.43-9.36 (m, 1H), 8.49 (d, J=2.2 Hz, 1H), 8.34-8.27 (m, 1H), 7.98-7.22 (m, 3H), 3.69-3.59 (m, 1H), 3.45-3.22 (m, 4H), 2.98-2.81 (m, 1H), 2.59-1.75 (m, 9H), 1.45-1.22 (m, 10H); ESI MS m/z 522 [C30H36ClN3O3+H]+; HPLC 95.2% (AUC), tR=10.26 min.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-87217b92e9ff468dbb73b9c32254d178
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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