Diisopropylethylamine → HCID 71212241, compound

HRID 1752242Notes

Reaction equation

HRID 1752242 reaction equation
[O:1]=[C:2]1[C@@H:6](OS(C)(=O)=O)[CH2:5][CH2:4][NH:3]1.Cl.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH:22]2[CH2:27][CH2:26][N:25]([CH:6]3[CH2:5][CH2:4][NH:3][C:2]3=[O:1])[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 14256265(S)-2-oxopyrrolidin-3-yl methanesulfonate

Product 1

HCID 71212241HCID 71212241, compoundYield 7.8%

Conditions

Temperature
85 °C

Procedure

To a 10 mL microwave vial was added methanesulfonic acid (S)-2-oxo-pyrrolidin-3-yl ester (4.97 mmol, 890 mg) and (4-fluoro-phenyl)-piperidin-4-yl-methanone hydrochloride (4.97 mmol, 1.21 g) in DIEA (24.8 mmol, 5 mL) was heated to 85° C. for 105 min. The DIEA was decanted and flash column chromatography (silica) was performed eluting with ethyl acetate to 20% MeOH/ethyl acetate afforded the title compound (112 mg, 7.8% yield). MS (ESI) m/e 291.2 (M+H+), calculated 290.33; 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=2.303 min.

Workup

  1. customThe DIEA was decanted
  2. washflash column chromatography (silica) was performed eluting with ethyl acetate to 20% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-3d040f74f12b4970b58a0ca6d3add2a7
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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