Diethylamine → HCID 58418005, compound

HRID 1908858Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:27]([NH:29][CH2:30][CH3:31])[CH3:28].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1>[CH2:27]([N:29]([CH2:30][CH3:31])[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1)[CH3:28]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-chloro-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (160 mg, 0.558 mmol, Example 43a)) in dioxane (10 mL), Cs2CO3 (636 mg, 1.95 mmol) and diethylamine (204 mg, 2.79 mmol) is added. The mixture is degassed and put under N2 before Pd(II) acetate (25 mg, 0.112 mmol) and Xantphos (116 mg, 0.201 mmol) is added. The mixture is stirred in a sealed vial at 90° C. for 72 h before it is cooled to rt. The mixture is filtered and the filtrate is evaporated. The crude product is purified on prep. TLC plates with heptane:EA 3:1 to give 2-diethylamino-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (43 mg) as a yellow solid; LC-MS: tR=0.66 min, [M+1]+=324.15; 1H NMR δ 1.26 (t, J=7.0 Hz, 6H), 2.51 (s, 3H), 2.71 (s, 3H), 3.63 (q, J=7.0 Hz, 4H), 7.01 (s, 1H), 7.09 (s, 1H), 7.86 (d, J=5.0 Hz, 1H), 7.94 (s, 1H), 8.71 (d, J=5.0 Hz, 1H).

Workup

customThe mixture is degassed
additionis added
temperatureis cooled to rt
filtrationThe mixture is filtered
customthe filtrate is evaporated
customThe crude product is purified on prep

Sources & evidence

ORD record: ord-ed8fdbe4d52145f1804168c9225f0b1b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598208B2

Reaction notes

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