Hydrogen Peroxide → HCID 56953577, compound

HRID 712258Notes

Reaction equation

HRID 712258 reaction equation
C([O:3][C:4]([C:6]1([CH3:36])[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20](B(O)O)[C:21]4[S:25][C:24]([NH:26][C:27](=[O:31])[NH:28][CH2:29][CH3:30])=[N:23][C:22]=4[CH:32]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.OO.S(=O)(=O)(O)[OH:40]>[OH-].[Na+].O>[CH2:29]([NH:28][C:27]([NH:26][C:24]1[S:25][C:21]2[C:20]([OH:40])=[CH:19][C:18]([C:15]3[CH:16]=[N:17][C:12]([N:9]4[CH2:8][CH2:7][C:6]([CH3:36])([C:4]([OH:3])=[O:5])[CH2:11][CH2:10]4)=[N:13][CH:14]=3)=[CH:32][C:22]=2[N:23]=1)=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 86663971HCID 86663971, compound

Product 1

HCID 56953577HCID 56953577, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A stirred suspension of [5-[2-(4-ethoxycarbonyl-4-methyl-1-piperidyl)pyrimidin-5-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-7-yl]boronic acid (166 mg, 0.286 mmol) in aqueous NaOH solution (2 M, 1.3 mL) was treated with excess hydrogen peroxide (27.5% aqueous solution, 0.45 mL) and kept at rt for 3 days by which time LCMS showed complete reaction. The resultant mixture was diluted with water (30 mL) and acidified by the addition of a small amount of conc. sulfuric acid. The precipitated solid was collected by filtration, washed with water (10 mL) and dried in vacuo to give Compound 26 as a white solid (102 mg, 78% yield). 1H NMR (DMSO-d6): δ 10.37 (1H, s), 8.67 (2H, s), 7.37 (1H, s), 6.85 (1H, s), 6.77 (1H, t, J=5.86 Hz), 4.30 (2H, dt, J=13.75, 4.56 Hz), 3.36 (2H, ddd, J=13.34, 9.92, 3.07 Hz), 3.22 (2H, p, J=6.69 Hz), 2.04 (2H, dt, J=13.63, 3.69 Hz), 1.42 (2H, ddd, J=13.55, 10.29, 3.91 Hz), 1.22 (3H, s), 1.13 (3H, t, J=7.19 Hz). m/z: 457 [M+H]+.

Workup

  1. customreaction
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water (10 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-08713fd4903a405fab61a1ac94bb26dd
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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