Phosphorus oxychloride → (4-[4-(6-Chloro-pyridazin-3-yl)-phenyl]-cyclohexyl)-acetic acid ethyl ester

HRID 1404266Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21](=O)[NH:20][N:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].P(Cl)(Cl)([Cl:28])=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][C:21]([Cl:28])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A 50 Ml flask was charged with {4-[4-(6-oxo-1,6-dihydro-pyridazin-3-yl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (0.76 g, 2.2 mmol, 1.0 equiv) in 20 Ml toluene followed by phosphorous oxychloride (0.62 Ml, 6.7 mmol, 3.0 equiv). The suspension was heated to 100° C., at which point a homogeneous solution ensued. The reaction was stirred overnight at 100° C., then cooled to room temperature. Removal of volatiles in vacuo afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.07-1.17 (m, 2 H) 1.20 (t, J=7.07 Hz, 3 H) 1.43-1.53 (m, 2 H) 1.78-1.90 (m, 5 H) 2.18 (d, J=6.57 Hz, 2 H) 2.44-2.52 (m, 1 H) 4.08 (q,J=7.07 Hz, 2 H) 7.29 (d, J=8.34 Hz, 2 H) 7.46 (d, J=9.09 Hz, 1 H) 7.72 (d, J=9.09 Hz, 1 H) 7.90 (d, J=8.59 Hz, 2 H); (M+H)+ 359.

Workup

temperaturecooled to room temperature
customRemoval of volatiles in vacuo

Sources & evidence

ORD record: ord-ac2d68f3bed2472e906749c51e6d2f88
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912208B2

Reaction notes

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