1,4-Dioxane hydrochloride → HCID 89477944, compound

HRID 1771156Notes

Reaction equation

HRID 1771156 reaction equation
C(=O)([O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][C:21](Cl)=[N:20]3)=[O:16])[C:9]=1[F:28])OC(C)(C)C.Cl.[O:31]1CCOC[CH2:32]1>CO>[F:28][C:9]1[C:8]([OH:7])=[CH:13][CH:12]=[C:11]([F:14])[C:10]=1[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][C:21]([O:31][CH3:32])=[N:20]2)=[O:16]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 89484872HCID 89484872, compound

Product 1

HCID 89477944HCID 89477944, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate (55 mg, 0.13 mmol, 1 eq.) in MeOH (5 mL) was added HCl/dioxane (3 N, 5 mL). The resulting mixture was stirred overnight, then concentrated. The residue was purified via flash column chromatography (PE/EA=1/1, v/v) to afford (2,6-difluoro-3-hydroxyphenyl)(3-methoxyquinoxalin-6-yl)methanone (20.3 mg, 49%). LCMS (M−H+) m/z calculated 315.1, found 315.0. 1H NMR (CD3OD, 400 MHz) δ 8.49 (s, 1 H), 8.01-8.06 (m, 3 H), 7.01-7.07 (m, 1 H), 6.86-6.91 (m, 1 H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via flash column chromatography (PE/EA=1/1

Sources & evidence

ORD record
ord-e8564e93d06b43ab89455438b2a23c61
Source dataset
uspto-grants-2016_02
Patent number
US09249111B2

Reaction notes

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