Pyridine → HCID 11710500, compound

HRID 1867306Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([CH:16]([CH3:18])[CH3:17])[C:5]=1[NH2:19])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH:26]1([CH2:31][C:32](Cl)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1>O1CCCC1.C(OCC)(=O)C>[CH:26]1([CH2:31][C:32]([NH:19][C:5]2[C:6]([CH:16]([CH3:18])[CH3:17])=[CH:7][C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:9][C:4]=2[CH:1]([CH3:3])[CH3:2])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2,6-diisopropyl-4-morpholin-4-yl-phenylamine (279 mg) and pyridine (245 μL) in tetrahydrofuran (2 mL) was added cyclopentylacetyl chloride (210 μL) and the mixture was stirred for 1 hour at 25° C. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with 10% aqueous sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Recrystallisation of the crude brown material from hot ethyl acetate/heptane furnished 122 mg (33%) of the title compound as a white solid. LC-MS (m/z) 373 (MH+); tR=2.58, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, CDCl3): 1.19 (d, 12H), 1.27 (m, 2H), 1.60 (m, 2H), 1.68 (m, 2H), 1.93 (m, 2H), 2.40 (m, 1H), 2.41 (m, 2H), 3.05 (m, 2H), 3.17 (m, 4H), 3.87 (m, 4H), 6.49 (s, 1H), 6.70 (s, 2H).

Workup

washwashed with 10% aqueous sodium bicarbonate (20 mL) and brine (20 mL)
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography
customRecrystallisation of the crude brown material from hot ethyl acetate/heptane

Sources & evidence

ORD record: ord-1eddba3a2df34bbbb16622948f64cc6f
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632835B2

Reaction notes

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