Cyclopentylacetyl chloride → 2-Cyclopentyl-N-(2-methyl-4-morpholin-4-yl-6-trifluoromethyl-phenyl)-acetamide

HRID 1867310Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([C:14]([F:17])([F:16])[F:15])[C:3]=1[NH2:18].[CH:19]1([CH2:24][C:25](Cl)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1>C(#N)C.C(OCC)(=O)C>[CH:19]1([CH2:24][C:25]([NH:18][C:3]2[C:4]([C:14]([F:17])([F:16])[F:15])=[CH:5][C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:7][C:2]=2[CH3:1])=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Methyl-4-morpholin-4-yl-6-trifluoromethyl-phenylamine (0.18 g) and cyclopentylacetyl chloride (112 mg) were dissolved in acetonitrile (4 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL) and brine (1×20 mL). The organic phase was dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 132 mg (52%) of the title compound as a white solid. LC-MS (m/z) 371 (MH+); tR=2.87, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.60 (m, 2H), 1.76 (m, 2H), 2.11 (s, 3H), 2.24 (m, 1H), 2.26 (d, 2H), 3.16 (t, 4H), 3.73 (t, 4H), 7.00 (d, 1H), 7.12 (d, 1H), 9.16 (s, 1H).

Workup

washwashed with water (2×20 mL) and brine (1×20 mL)
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography

Sources & evidence

ORD record: ord-6046a84946bc48c588bdeca1a350e0eb
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632835B2

Reaction notes

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