Ethanol hydrochloride → Hydrochloric Acid
Reaction equation
[NH2:1][C:2]1[C:3]([C:16]2[CH:36]=[CH:35][C:19]([C:20]([NH:22][C@@H:23]([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([Br:34])[CH:28]=3)[CH2:24][NH:25][CH3:26])=[O:21])=[C:18]([F:37])[CH:17]=2)=[N:4][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([OH:14])[C@@H:10]([F:15])[CH2:9]2)=[CH:6][N:7]=1.C(O)C.[ClH:41]>>[ClH:41].[NH2:1][C:2]1[C:3]([C:16]2[CH:36]=[CH:35][C:19]([C:20]([NH:22][C@@H:23]([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([Br:34])[CH:28]=3)[CH2:24][NH:25][CH3:26])=[O:21])=[C:18]([F:37])[CH:17]=2)=[N:4][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([OH:14])[C@@H:10]([F:15])[CH2:9]2)=[CH:6][N:7]=1Participants
Procedure
The HCl salt form of 4-(3-amino-6-((1 S,3S,4S)-3-fluoro-4-hydroxycyclohexyl)pyrazin-2-yl)-N—((S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl)-2-fluorobenzamide was prepared by dissolving amorphous 4-(3-amino-6-((1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl)pyrazin-2-yl)-N—((S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl)-2-fluorobenzamide (120 mg) in 0.5N HCl ethanol solution (414 μL) with stirring at room temperature. A precipitate is observed after 5 minutes of stirring. A DSC/TGA thermograph of the highly crystalline HCl salt form of 4-(3-amino-6-((1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl)pyrazin-2-yl)-N—((S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl)-2-fluorobenzamide is provided in FIG. 4. An X-ray powder diffraction pattern of the free base form was determined in FIG. 3. The most significant peaks in the XRPD of FIG. 3 are shown in the table:
Workup
- customThe HCl salt form of 4-(3-amino-6-((1 S,3S,4S)-3-fluoro-4-hydroxycyclohexyl)pyrazin-2-yl)-N—((S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl)-2-fluorobenzamide was prepared
- stirringof stirring
Sources & evidence
- ORD record
- ord-55f2510e201b4fe2ae367fa5b97e80ea
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242996B2
Reaction notes
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