Potassium Hydroxide → HCID 16123323, compound

HRID 1882214Notes

Reaction equation

HRID 1882214 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:17]3[C:18]4[CH:24]=[C:23]([CH3:25])[CH:22]=[N:21][C:19]=4[NH:20][C:16]=3[C:15]([C:26]#[N:27])=[N:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[OH-:28].[K+]>C1COCC1.OO>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[C:17]3[C:18]4[CH:24]=[C:23]([CH3:25])[CH:22]=[N:21][C:19]=4[NH:20][C:16]=3[C:15]([C:26]([NH2:27])=[O:28])=[N:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 16123322HCID 16123322, compound

Product 1

HCID 16123323HCID 16123323, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 48 (10 mg, 0.027 mmol) stirred in THF (1 mL). A solution of KOH (25 mg, 0.44 mmol) in 30% H2O2 (0.5 mL) was added, and the reaction stirred for 3 h at r.t. Purification by prep-HPLC gave 8.2 mg (77%) of the title compound as an off-white solid. 1H NMR (400 MHz, MeOD-d4): δ 8.49 (br s, 1H), 8.41 (s, 1H), 8.26 (s, 1H), 8.15 (d, 1H, J=7.6 Hz), 8.06 (d, 1H, J=7.6 Hz), 7.92 (t, 1H, J=7.6 Hz), 7.85 (s, 1H), 3.32 (q, 2H, J=7.2 Hz), 2.39 (s, 3H), 1.31 (t, 3H, J=7.6 Hz). MS (ES) [m+H] calc'd for C20H18N4O3S, 395; found 395.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-fa18d131c20c43df99894f5d95be2d67
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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