Diisopropylethylamine → HCID 71212188, compound

HRID 1752243Notes

Reaction equation

[O:1]=[C:2]1[C@@H:6](OS(C)(=O)=O)[CH2:5][CH2:4][NH:3]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH:21]2[CH2:26][CH2:25][N:24]([CH:6]3[CH2:5][CH2:4][NH:3][C:2]3=[O:1])[CH2:23][CH2:22]2)=[O:20])=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 27771154-(4-Chlorobenzoyl)Piperidine

HCID 14256265(S)-2-oxopyrrolidin-3-yl methanesulfonate

Product 1

HCID 71212188HCID 71212188, compoundYield 31%

Conditions

Temperature: 85 °C

Procedure

A 10 mL microwave vial containing methanesulfonic acid (S)-2-oxo-pyrrolidin-3-yl ester (0.56 mmol, 100 mg) and (4-chloro-phenyl)-piperidin-4-yl-methanone (0.56 mmol, 125 mg) in DIEA (2.8 mmol, 0.5 mL) was heated to 85° C. for 105 min. The diisopropylethylamine was decanted off and flash column chromatography (silica) was performed eluting with ethyl acetate to 20% MeOH/ethyl acetate afforded the title compound (53 mg, 31% yield). MS (ESI) m/e 307.3 (M+H+), calculated 306.2; HPLC (Novapak 150×3.9 mm C18 column: mobile phase: 10-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 5 min.) retention time=2.506 min.

Workup

customThe diisopropylethylamine was decanted off
washflash column chromatography (silica) was performed eluting with ethyl acetate to 20% MeOH/ethyl acetate

Sources & evidence

ORD record: ord-f427375f05234234b870b9bc4ccbd761
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163003B2

Reaction notes

Loading…