Hydrochloric Acid → HCID 59587547, compound

HRID 389733Notes

Reaction equation

HRID 389733 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[CH:31][NH:32]3)[O:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(=[O:3])[NH2:2].Cl.O1CCOCC1>C(Cl)Cl.CO>[NH:32]1[C:33]2[C:29](=[C:28]([C:6]3[O:7][C:8]([C:9]4[CH:10]=[CH:11][C:12]([N:15]5[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]5)=[CH:13][CH:14]=4)=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=3)[CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:31]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68775331HCID 68775331, compound

Product 1

HCID 59587547HCID 59587547, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 4-(4-(4-carbamoyl-2-(1H-indol-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.027 g, 0.06 mmol) in DCM (1 ml) was added 4M HCl in dioxane (0.5 ml, 2.0 mmol) and the reaction stirred at room temperature for 2 hours. The mixture was then diluted with MeOH and purified by SPE using a MP-TsOH cartridge (500 mg) to afford 2-(1H-indol-4-yl)-5-(4-(piperazin-1-yl)phenyl)oxazole-4-carboxamide (0.0078 g, 0.02 mmol, 36%). 1H NMR (DMSO) δ 2.86 (4H, br. t), 3.22 (4H, br. t), 7.06 (2H, d), 7.21 (1H, t), 7.35 (1H, br. t), 7.56-7.60 (2H, m), 7.62 (1H, d), 7.79 (1H, br. s), 7.86 (1H, dd), 8.30 (2H, d), 11.51 (1H, br. s). LCMS (2) Rt: 2.36 min; m/z (ES+) 388.

Workup

  1. custompurified by SPE

Sources & evidence

ORD record
ord-a4ce5816bce04ce3b8eaea23bca05e4a
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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