Triethylamine → 3-{6-Chloro-2-fluoro-3-[4-(4-methyl-piperazin-1-yl)-4-oxo-butyl]-benzyl}-1-cyclohexyl-pyrrolidin-2-one

HRID 2235259Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([F:14])[C:3]=1[CH2:15][CH:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:17]1=[O:27].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:56][N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:15][CH:16]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[C:17]2=[O:27])=[C:4]([F:14])[C:5]([CH2:8][CH2:9][CH2:10][C:11]([N:60]2[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]2)=[O:13])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 4-[4-chloro-3-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-2-fluoro-phenyl]-butyric acid (Preparation 80) (200 mg, 0.22 mmol), EDAC (63 mg, 0.33 mmol), HOBT (45, mg, 0.33 mmol), triethylamine (0.1 mL, 0.7 mmol) and 1-methylpiperazine (0.1 mL, 0.9 mmol) in THF (5 mL). Heat the mixture at 80° C. for 3 hours. Evaporate solvent and purify the residue by column chromatography to give the title product as white solid: Mass spectrum (ion spray): m/z=478.3 (M+H).

Workup

customEvaporate solvent and purify the residue by column chromatography

Sources & evidence

ORD record: ord-7c020e8ca6df48d5acedaf93ed7f9857
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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