1,4-Dioxane → HCID 59587537, compound

HRID 389717Notes

Reaction equation

HRID 389717 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-d9b8684316544853b3be98b1e641266e
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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