m-Chloroperbenzoic acid → HCID 178513872, compound

HRID 1508747Notes

Reaction equation

HRID 1508747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH2:27])=[O:26])=[CH:20][CH:19]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[NH2:27][C:25](=[O:26])[CH2:24][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:10]2[CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N+:13]([O-:36])=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]=23)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 742209062-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetamide

Product 1

HCID 178513872HCID 178513872, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetamide (0.070 g, 0.18 mmol) in chloroform (20 mL) at rt was added MCPBA (77%, 0.062 g, 0.28 mmol). The mixture stirred at rt for 16 h and then purified by preparative HPLC (water/acetonitrile with 0.05% TFA) to afford the title compound (0.017 g, 23%) as a white solid. MW=393.87. 1H NMR (DMSO-d6, 500 MHz) δ 9.52 (s, 1H), 7.76-7.73 (m, 1H), 7.64-7.60 (m, 1H), 7.59-7.52 (m, 2H), 7.47 (s, 1H), 7.36-7.26 (m, 4H), 6.88 (s, 1H), 6.83 (s, 1H), 3.38 (s, 2H), 3.19 (t, J=7.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.25 (quin, J=7.5 Hz, 2H); APCI MS m/z 394 [M+H]+.

Workup

  1. custompurified by preparative HPLC (water/acetonitrile with 0.05% TFA)

Sources & evidence

ORD record
ord-91ba2fbd883941a988a9cd29f404fca6
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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