Hydrochloric Acid → Afuresertib Hydrochloride

HRID 1913378Notes

Reaction equation

HRID 1913378 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:12][C:13]([C:15]1[S:16][C:17]([Cl:27])=[C:18]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2[Cl:26])[CH:19]=1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1.Cl>O1CCOCC1>[ClH:26].[NH2:1][CH2:2][C@@H:3]([NH:12][C:13]([C:15]1[S:16][C:17]([Cl:27])=[C:18]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2[Cl:26])[CH:19]=1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46843057Afuresertib2×

Product 1

HCID 46843056Afuresertib Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The hydrochloride salt of N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide prepared generally as described in Example 96 of International Application No. PCT/US2008/053269, having an International Filing date of Feb. 7, 2008, and having International Publication Number WO/2008/098104 and an International Publication Date of Aug. 14, 2008, which generally states that the free base compound, N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide, is treated with 4M HCl in dioxane and after 5 min, the solution is concentrated and dried under vacuum to afford N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride, yielded an amorphous solid as indicated by the Powder X-Ray Diffraction (PXRD) pattern depicted in FIG. 3.

Workup

  1. concentrationthe solution is concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-fb6f7b16b33a4176b067878ea8fbb74b
Source dataset
uspto-grants-2013_12
Patent number
US08609711B2

Reaction notes

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