1,4-Dioxane → HCID 59587537, compound

HRID 714950Notes

Reaction equation

HRID 714950 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-777b89df2fb544aeaf538b3c1f4bdd15
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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