Hydrochloric Acid → HCID 66615892, compound

HRID 1404267Notes

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[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].Cl>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:7][CH2:8][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][C:21]([NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[C:27]([Cl:26])[CH:28]=4)=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of {4-[4-(6-chloro-pyridazin-3-yl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (2.0 g, 5.6 mmol, 1.0 equiv) in 40 Ml dioxane was added 3-chloroaniline (0.70 Ml, 6.7 mmol, 1.2 equiv) followed by 2 Ml 4 N HCl in dioxane. The mixture was then heated to 100° C. overnight. The reaction was partitioned between EtOAc and saturated bicarbonate solution, and the organic extracts were then washed with brine and dried. Removal of solvent in vacuo afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.07-1.17 (m, 2 H) 1.21 (t, J=7.20 Hz, 3 H) 1.42-1.53 (m, 2 H) 1.86 (t, J=10.99 Hz, 4 H) 1.78-1.90 (m, 1 H) 2.18 (d, J=6.57 Hz, 2H) 2.47 (td, J=12.00, 3.03 Hz, 1 H) 4.08 (q, J=7.24 Hz, 2 H) 7.03 (d, J=7.58 Hz, 1 H) 7.26 (d, J=8.08 Hz, 3 H) 7.20-7.28 (m, 2 H) 7.45 (s, 1 H) 7.68 (d, J=9.35 Hz, 1 H) 7.84 (d, J=8.34 Hz, 2 H); (M+H)+ 450.2.

Workup

customThe reaction was partitioned between EtOAc and saturated bicarbonate solution
washthe organic extracts were then washed with brine
customdried
customRemoval of solvent in vacuo

Sources & evidence

ORD record: ord-ca65fe4a9caf48d8a5367d76b11db9d5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912208B2

Reaction notes

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