4-tert-Butylbenzylamine → HCID 67273904, compound

HRID 598222Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of ethyl 2-chloro-3-pyridinecarboxylate (0.610 g, 3.29 mmol) in ethanol (10.0 mL) was treated with 4-tert-butylbenzylamine (0.580 mL, 3.29 mmol). The mixture was heated to 160° C. for 1 h in a Biotage Initiator microwave synthesizer. The solution was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via flash column chromatography (20-60% ethyl acetate in hexanes) afforded the title compound clear yellow oil (0.461 g, 45%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.34 (dd, J=4.8, 1.8 Hz, 1H), 8.18 (dd, J=7.8, 2.0 Hz, 1H), 7.30-7.42 (m, 4H), 6.58 (dd, J=7.6, 4.8 Hz, 1H), 4.75 (d, J=5.6 Hz, 2H), 4.34 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), 1.34 (s, 9H). MS(ES+) m/e 313 [M+H]+.

Workup

washwashed with saturated aqueous sodium bicarbonate
dry with materialThe organic portion was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via flash column chromatography (20-60% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-8137b0e5ae1b4204b79240816017ff67
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897612B2

Reaction notes

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