Hydrochloric Acid → Hydrochloric Acid

HRID 64004Notes

Reaction equation

HRID 64004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24]([N:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[C@@H:28]([CH3:39])[CH2:27]3)=[O:25])=[C:16]2[N:15]=1.[ClH:40]>>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24]([N:26]3[CH2:31][CH2:30][NH:29][C@@H:28]([CH3:39])[CH2:27]3)=[O:25])=[C:16]2[N:15]=1.[ClH:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46188930(S)-tert-butyl 4-(5-((R)-2-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-ylcarbamoyl)-2-methylpiperazine-1-carboxylate

Product 2

HCID 313Hydrochloric AcidHCID 67329857(S)-N-(5-((R)-2-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methylpiperazine-1-carboxamide hydrochloride

Procedure

To (S)-tert-butyl 4-(5-((R)-2-(2-chloro-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-ylcarbamoyl)-2-methylpiperazine-1-carboxylate (Example 24; 47 mg, 0.084 mmol), was added 1 mL 4 N HCl (dioxane) solution and stirred at ambient temperature for 10 minutes. The reaction was concentrated, treated with ether, and filtered, giving the final product HCl salt as a fine beige powder. MS (apci) m/z=458.1 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. additiontreated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-005464fbe477441cbd5a28e6525bf831
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

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