Cyclopentylacetyl chloride → HCID 11844985, compound

HRID 1158621Notes

Reaction equation

[CH3:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:3]=1.[CH:16]1([CH2:21][C:22](Cl)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[CH:16]1([CH2:21][C:22]([NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:5][C:6]=2[CH3:9])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 150 °C

Procedure

2,4-Dimethyl-6-morpholin-4-yl-pyridin-3-ylamine (0.22 g) and cyclopentylacetyl chloride (0.19 mL) were dissolved in acetonitrile (5 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo and purified by flash chromatography (SiO2, heptane/ethylacetate 3:1) to furnish 0.17 g (49% yield) of the title compound as a white solid. LC-MS (m/z) 318 (MH+); tR=1.40, (UV, ELSD) 97%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.21 (m, 2H), 1.52 (m, 2H), 1.61 (m, 2H), 1.77 (m, 2H), 2.05 (s, 3H), 2.17 (s, 3H), 2.24 (m, 1H), 2.26 (m, 2H), 3.37 (m, 4H), 3.67 (m, 4H), 6.53 (s, 1H), 9.05 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by flash chromatography (SiO2, heptane/ethylacetate 3:1)

Sources & evidence

ORD record: ord-43cb960ad8de4cd9a9423817244179f4
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812020B2

Reaction notes

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