Hydrochloric Acid → HCID 178458759, compound

HRID 2271785Notes

Reaction equation

HRID 2271785 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:23])[CH2:21][CH3:22])=[C:13]3[NH:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([CH2:31][N:32]([CH3:34])[CH3:33])[CH2:27][CH2:26]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].[ClH:35]>CO.ClCCl>[ClH:1].[ClH:35].[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:23])[CH2:21][CH3:22])=[C:13]3[NH:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([CH2:31][N:32]([CH3:34])[CH3:33])[CH2:27][CH2:26]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178458758HCID 178458758, compound

Product 1

HCID 178458759HCID 178458759, compoundYield 190.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(6-(3,5-dichloro-4-hydroxyphenyl)-4-((trans-4-((dimethylamino)methyl)cyclohexyl)amino)quinolin-3-yl)propan-1-one (3.75 g, 7.49 mmol) in methanol (150 mL) and dichloromethane (150 mL) was added HCl (1.25 M in methanol, 30 mL, 37.5 mmol). The solution was allowed to stir for 5 min, then concentrated under reduced pressure. The resultant solid was triturated with dichloromethane (25 mL), then dried under vacuum at 85° C. to afford the desired product (4.1 g, 95%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.12 (br s, 1H), 8.47 (br s, 1H), 8.26 (dd, J=8.7, 1.8 Hz, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.73 (s, 2H), 4.51 (br s, 1H), 3.18 (q, J=7.2 Hz, 2H), 3.09 (d, J=6.5 Hz, 2H), 2.93 (s, 6H), 2.45 (d, J=12.3 Hz, 2H), 2.11-2.02 (m, 3H), 1.88-1.76 (m, 2H), 1.40-1.30 (m, 2H), 1.24 (t, J=7.1 Hz, 3H). APCI MS m/z 500 [C27H31C12N3O2+H]+; HPLC>99% (AUC), tR=8.99 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resultant solid was triturated with dichloromethane (25 mL)
  3. customdried under vacuum at 85° C.

Sources & evidence

ORD record
ord-29eaabb9467748aebb06860a73e0e9b9
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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