Hydrochloric Acid → Morpholino(2-(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazol-4-yl)methanone dihydrochloride

HRID 1487795Notes

Reaction equation

HRID 1487795 reaction equation
[ClH:1].O1CCOCC1.[N:8]1([C:14]([C:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH:22]3[CH2:34][O:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[S:19][CH:20]=2)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>CO>[ClH:1].[ClH:1].[O:11]1[CH2:12][CH2:13][N:8]([C:14]([C:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH:22]3[CH2:34][O:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[S:19][CH:20]=2)=[O:15])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66797341Tert-butyl 4-(4-(morpholine-4-carbonyl)thiazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Product 1

HCID 66796562Morpholino(2-(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazol-4-yl)methanone dihydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(4-(morpholine-4-carbonyl)thiazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (35.4 mg, 0.0723 mmol) in MeOH (1 mL). After stirring overnight, the reaction mixture was concentrated under reduced pressure, yielding 33.2 mg (99%) of the title compound. LC-MS: RT=2.33 min, (M+H)+=390.6.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f27612fe3c1f4e0d9c1ec989422ccb57
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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