HCID 63089857, compound → HCID 118037253, compound

HRID 1508764Notes

Reaction equation

HRID 1508764 reaction equation
Cl.Cl[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:6]=[C:5]2[CH2:16][CH2:17][CH2:18][C:4]=12.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:23][CH:22]=1>CN1C(=O)CCC1>[Cl:15][C:11]1[CH:10]=[C:9]([C:7]2[N:6]=[C:5]3[CH2:16][CH2:17][CH2:18][C:4]3=[C:3]([N:20]([CH3:19])[C:21]3[CH:22]=[CH:23][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:25][CH:26]=3)[CH:8]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 63089857HCID 63089857, compoundHCID 901118224-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine HCl salt

Product 1

HCID 118037253HCID 118037253, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine hydrochloride (0.060 g, 0.20 mmol) and 2-(4-(methylamino)phenyl)acetamide (0.066 g, 0.40 mmol) in NMP (3 mL) was microwaved for 3 h at 140° C. After this time, the mixture was purified by silica gel chromatography followed by preparative HPLC to afford the title compound (0.012 g, 15%) as a white solid. MW=391.89. 1H NMR (DMSO-d6, 500 MHz) δ 14.18 (br s, 1H), 8.10 (s, 1H), 7.94 (d, J=7.5 Hz, 1H), 7.70-7.66 (m, 2H), 7.55 (br s, 7.37-7.27 (m, 5H), 6.92 (br s, 1H), 3.57 (s, 3H), 3.01 (t, J=7.1 Hz, 2H), 1.96-1.85 (m, 4H); ESI MS m/z 392 [M+H]+.

Workup

  1. customwas microwaved for 3 h at 140° C
  2. customAfter this time, the mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-96397827f3f940f4af576557ec7284b8
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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