Hydrochloric Acid → 2-(o-Toluidino)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamide

HRID 389764Notes

Reaction equation

HRID 389764 reaction equation
[C:1]1([CH3:35])[C:2]([NH:7][C:8]2[O:9][C:10]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[C:11]([C:13](=[O:15])[NH2:14])[N:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.Cl.O1CCOCC1>C(Cl)Cl.CO>[C:1]1([CH3:35])[C:2]([NH:7][C:8]2[O:9][C:10]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[C:11]([C:13]([NH2:14])=[O:15])[N:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59587624Tert-butyl 4-(4-(2-(o-toluidino)-4-carbamoyloxazol-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 595874062-(o-Toluidino)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(2-(o-toluidino)-4-carbamoyloxazol-5-yl)phenyl)piperazine-1-carboxylate (0.012 g, 0.025 mmol) in DCM (0.5 ml) was added 0.5M HCl in dioxane (0.25 ml, 0.125 mmol) and the resulting solution stirred at room temperature for 2 hours. The mixture was then diluted with MeOH and purified by SPE using a MP-TsOH (500 mg) cartridge to afford 2-(o-toluidino)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamide (0.0087 g, 0.023 mmol, 92%). 1H NMR (DMSO) δ 2.30 (3H, s), 2.84 (4H, m), 3.15 (4H, m), 6.97-7.01 (3H, m). 7.19-7.23 (2H, m), 7.32 (1H, br. d), 7.41 (1H, br. d), 7.99 (1H, dd), 8.07 (2H, d), 9.26 (1H, s). LCMS (2) Rt: 2.32 min; m/z (ES+) 378.

Workup

  1. custompurified by SPE

Sources & evidence

ORD record
ord-e4606168b519494fad935ea4dd89b541
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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