Hydrochloric Acid → HCID 66797762, compound

HRID 1487801Notes

Reaction equation

HRID 1487801 reaction equation
[ClH:1].O1CCOCC1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]2[CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:18])=[CH:12][CH:11]=1>>[ClH:1].[ClH:1].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH:20]2[CH2:32][C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:18])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671607Tert-butyl 4-(4-methoxyphenylcarbamoyl)-3-(pyridin-3-ylmethyl)piperazine-1-carboxylate

Product 1

HCID 66797762HCID 66797762, compoundYield 54%

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to tert-butyl 4-(4-methoxyphenylcarbamoyl)-3-(pyridin-3-ylmethyl)piperazine-1-carboxylate (76.0 mg, 0.141 mmol). After stirring overnight, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The desired chromatography fractions were concentrated under reduced pressure, dissolved in MeOH (1 mL), and treated with 4 M HCl in 1,4-dioxane (6 mL). This was concentrated under reduced pressure, yielding 30.5 mg (54%) of the desired product as an off-white solid. LC-MS: RT=2.11 min, [M+H]+=327.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
  3. concentrationThe desired chromatography fractions were concentrated under reduced pressure
  4. dissolutiondissolved in MeOH (1 mL)
  5. additiontreated with 4 M HCl in 1,4-dioxane (6 mL)
  6. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-33284714fb5647e88dd1f09c0b6cde1e
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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