Hydrochloric Acid → 1-[5-(4-Amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride

HRID 1189431Notes

Reaction equation

HRID 1189431 reaction equation
N#N.C(OC(=O)[NH:9][C:10]1[N:11]=[C:12]([CH2:15][C:16]2[O:17][C:18]([C:21](=[O:23])[CH3:22])=[CH:19][CH:20]=2)[S:13][CH:14]=1)(C)(C)C.[ClH:25]>C(Cl)Cl.O1CCOCC1>[ClH:25].[NH2:9][C:10]1[N:11]=[C:12]([CH2:15][C:16]2[O:17][C:18]([C:21](=[O:23])[CH3:22])=[CH:19][CH:20]=2)[S:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 67128535[2-(5-Acetyl-furan-2-ylmethyl)-thiazol-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 671287161-[5-(4-Amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(5-acetyl-furan-2-ylmethyl)-thiazol-4-yl]-carbamic acid tert-butyl ester (167 mg, 0.52 mmol) in dry CH2Cl2 (5.2 mL) was treated at 0° C. with HCl (1.3 mL of a 4M solution in dioxane, 5.18 mmol). After stirring at 0° C. for 1 h, the reaction mixture was stirred at rt for 16 h. The solvents were removed under reduced pressure to give the title compound. LC-MS-conditions 02: tR=0.65 min, [M+H]+=223.36.

Workup

  1. stirringthe reaction mixture was stirred at rt for 16 h
  2. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-229687e64b77472e842131176cb9588d
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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