m-Chloroperbenzoic acid → HCID 68991679, compound

HRID 2381548Notes

Reaction equation

HRID 2381548 reaction equation
[CH:1]1([CH2:6][CH:7]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([S:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=[N:22]2)[C:8]([NH:10][C:11]2[CH:15]=[CH:14][N:13]([CH2:16][C:17]([OH:20])([CH3:19])[CH3:18])[N:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:43])C=1>O1CCCC1>[C:29]1([S:28]([C:24]2[CH:23]=[N:22][N:21]([CH:7]([CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([NH:10][C:11]3[CH:15]=[CH:14][N:13]([CH2:16][C:17]([OH:20])([CH3:19])[CH3:18])[N:12]=3)=[O:9])[C:26](=[O:27])[CH:25]=2)=[O:43])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 44464555HCID 44464555, compound2×

Product 1

HCID 68991679HCID 68991679, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(6-oxo-4-phenylsulfanyl-6H-pyridazin-1-yl)-propionamide (30 mg, 0.06 mmol) in tetrahydrofuran (1 mL) was treated with m-chloroperbenzoic acid (10.8 mg, 0.06 mmol). In a separate flask, a solution of 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(6-oxo-4-phenylsulfanyl-6H-pyridazin-1-yl)-propionamide (30 mg, 0.06 mmol) in tetrahydrofuran (1 mL) was treated with m-chloroperbenzoic acid (21.5 mg, 0.12 mmol). Both reactions were stirred at 25° C. for 3 nights. At this time, each reaction was individually concentrated in vacuo. Two separate HPLC purifications (30-100% acetonitrile/water, C18 Pursuit Agilient, 20×150mm, 30 ml/min) were combined to afford 2-(4-benzenesulfinyl-6-oxo-6H-pyridazin-1-yl)-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide (6.9 mg, 11%) as a white solid; ES+-HRMS m/e calcd for C25H31N5O4S [M+H+] 498.2170 found 498.2171. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (2×s, 6H), 1.19-1.70 (m, 9H), 1.88-2.01 (m, 1H), 2.10-2.26 (m, 1H), 3.87 (s, 2H), 4.66 (s, 1H), 5.47 (dd, J=10.6, 4.2 Hz, 1H), 6.35 (d, J=2.4 Hz, 1H), 7.51 (dd, J=2.4 Hz, 1H), 7.54 (dd, J=2.4 Hz, 1H), 7.73 (t, J=7.5 Hz, 2H), 7.85 (t, J=7.5 Hz, 1H), 8.14 (d, J=7.5 Hz, 2H), 8.47 (d, J=2.4 Hz, 1H), 10.87 (s, 1H); and 2-(4-benzenesulfonyl-6-oxo-6H-pyridazin-1-yl)-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide (14.9 mg, 23%) as a white solid; ES+-HRMS m/e calcd for C25H31N5O5S [M+H+] 514.2119 found 514.2121. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (s, 3H), 1.04 (s, 3H), 1.20-1.70 (m, 9H), 1.86-2.02 (m, 1H), 2.07-2.31 (m, 1H), 3.87 (s, 2H), 4.66 (s, 1H), 5.47 (dd, J=10.4, 4.4 Hz, 1H), 6.35 (d, J=2.4 Hz, 1H), 7.51 (d, J=2.4 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.73 (t, J=7.5 Hz, 2H), 7.85 (t, J=7.5 Hz, 1H), 8.14 (d, J=7.5 Hz, 2H), 8.47 (d, J=2.4 Hz, 1H), 10.87 (s, 1H).

Workup

  1. concentrationAt this time, each reaction was individually concentrated in vacuo
  2. customTwo separate HPLC purifications (30-100% acetonitrile/water, C18 Pursuit Agilient, 20×150mm, 30 ml/min)

Sources & evidence

ORD record
ord-f190cbfae57e4e0bb32148c453b0a575
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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