Hydrochloric Acid → HCID 18956279, compound

HRID 2379888Notes

Reaction equation

HRID 2379888 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17][C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)=[O:19])[N:11]=2)[N:9]=1)[NH2:3].Cl>O1CCCC1>[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17][C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[O:19])[N:11]=2)[N:9]=1)[NH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18956296HCID 18956296, compound

Product 1

HCID 18956279HCID 18956279, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(diaminomethyleneamino)-4-[6-(1-tert-butoxycarbonylpiperidin-3-yl)carbonylaminomethylpyridin-2-yl]thiazole (1.9 g) and 4N-methanolic hydrogen chloride (40 ml) was stirred for 7 hours at ambient temperature. To the reaction mixture was added a tetrahydrofuran (40 ml) and the isolated precipitate was collected by filtration. The precipitate was added to water and adjusted to pH 13 with 5N-sodium hydroxide. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-(diaminomethyleneamino)-4-[6-(3-piperidyl)carbonylaminomethylpyridin-2-yl]thiazole (0.47 g).

Workup

  1. filtrationthe isolated precipitate was collected by filtration
  2. additionThe precipitate was added to water
  3. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-72f2bf314475498cae3ae0f097c7aeb4
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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