m-Chloroperbenzoic acid → HCID 57744447, compound

HRID 1887374Notes

Reaction equation

HRID 1887374 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[S:10][C:11]([C:15]([NH:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:12]([CH3:14])[N:13]=2)[C:5](=[O:25])[CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:31]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[S:10][C:11]([C:15]([NH:17][CH2:18][C:19]3[CH:20]=[N+:21]([O-:31])[CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:12]([CH3:14])[N:13]=2)[C:5](=[O:25])[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 24984278HCID 24984278, compound

Product 1

HCID 57744447HCID 57744447, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(4-methoxy-2-oxopyridin-1(2H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.10 g, 0.28 mmol) in anhydrous dichloromethane (10 mL) was added m-chloroperoxy benzoic acid (0.072 g, 0.42 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 24 hours, diluted with dichloromethane (100 mL), washed with saturated bicarbonate solution (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was crystallized in ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexane to afford the title compound as a colorless solid in 34% yield (0.035 g): mp 255-257° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.81 (t, J=5.8 Hz, 1H), 8.59 (d, J=8.1 Hz, 1H), 8.13 (s, 1H), 8.09 (d, J=6.3 Hz, 1H), 7.37-7.23 (m, 2H), 6.33 (dd, J=8.1, 2.7 Hz, 1H), 6.12 (d, J=2.7 Hz, 1H), 4.34 (d, J=5.7 Hz, 2H), 3.81 (s, 3H), 2.54 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 168.6, 162.2, 161.7, 154.1, 151.0, 139.3, 138.1, 137.7, 131.9, 126.7, 124.9, 123.0, 104.2, 96.5, 56.8, 42.1, 17.5; MS (ES+) m/z 373.3 (M+1), 395.2 (M+23).

Workup

  1. washwashed with saturated bicarbonate solution (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized in ethyl acetate
  6. filtrationThe solid was collected by filtration
  7. washwashed with methanol and hexane

Sources & evidence

ORD record
ord-137ebb2e6220484cbfbf63fcaf16fe32
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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