1,4-Dioxane → HCID 59587537, compound

HRID 1410449Notes

Reaction equation

HRID 1410449 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=2[F:35])[O:7][C:8]=1[C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)(=[O:3])[NH2:2].O1CCOCC1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl.Cl>[F:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=1[C:6]1[O:7][C:8]([C:9]2[CH:14]=[N:13][C:12]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[CH:11][CH:10]=2)=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 46206217HCID 46206217, compound

Product 1

HCID 59587537HCID 59587537, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(5-(4-carbamoyl-2-(2,6-difluorophenyl)oxazol-5-yl)pyridin-2-yl)piperazine-1-carboxylate (0.227 g, 0.47 mmol) in DCM (3 mL) and 4N HCl in dioxane (2 mL, 8.0 mmol) was stirred at room temperature for 48 hours. The solvent was removed in vacuo to give 2-(2,6-difluorophenyl)-5-(6-(piperazin-1-yl)pyridin-3-yl)oxazole-4-carboxamide (0.211 g, 0.46 mmol, 98%) as a white solid as the dihydrochloride salt. 1H NMR (DMSO) 3.20 (4H, m), 3.90 (4H, t), 7.11 (1H, d), 7.39 (2H, t), 7.73 (3H, m), 8.44 (1H, dd), 9.0 (1H, d), 9.24 (1H, br. s), 9.30 (1H, br. s). LCMS (2) Rt: 2.38 min; m/z (ES+) 386.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fb08eb1dec4549bfb15ef5c769c07080
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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