Hydrochloric Acid → HCID 53322397, compound

HRID 333292Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13][C:12]([CH3:16])([OH:15])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:21](O)[CH3:22].Cl>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][N:18]([CH3:19])[CH3:20])[CH2:10][CH2:11][C:12]([CH3:16])([OH:15])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:17][NH:18][CH2:21][CH3:22])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 3-L, three-neck flask equipped with a temperature probe, nitrogen line and overhead stirrer was charged with free base of 277 (crude from previous reaction, 0.328 mol) and ethanol (500 mL). The mixture was heated to 50° C. until a clear solution was obtained. The solution was cooled to room temperature and added to a solution of 2 M HCl in ether (200 mL) slowly. After 5 min, precipitation of HCl salt was observed. The slurry was stirred for 1 h at room temperature and filtered. The cake was washed with a mixture of MTBE/EtOH (2:1, 200 mL) and dried over night under high vacuum to yield 277 hydrochloride [80.8 g, 70%, 98.0% (AUC) by HPLC]. 1H NMR (D2O, 300 MHz): δ 7.65 (d, 1H), 7.55 (d, 1H), 7.5 (dd, 1H), 3.5 (s, 2H), 2.5 (s, 6H), 2.15 (dd, 2H), 1.85 (dt, 2H), 1.5 (dd, 2H), 1.3 (dt, 2H), 0.05 (s, 3H).

Workup

customwas obtained
temperatureThe solution was cooled to room temperature
customprecipitation of HCl salt
filtrationfiltered
washThe cake was washed with a mixture of MTBE/EtOH (2:1, 200 mL)
customdried over night under high vacuum

Sources & evidence

ORD record: ord-06f13ff9960c43159439756151e10185
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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