Triethylamine → Ethyl (cis)-2-[(6-chloropyridazin-4-yl)amino]cyclohexanecarboxylate

HRID 510191Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.Cl.[NH2:10][C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

3,5-dichloropyridazine (1.6 g, 10.74 mmol), ethyl (cis)-2-aminocyclohexanecarboxylate hydrochloride (CA, 2.454 g, 11.81 mmol), and triethylamine (5.63 mL, 32.2 mmol) were added to DMSO (10.0 ml) and heated for 5 hrs at 120° C. and then allowed to stir at room temperature for 24 hr. Solvents were removed in vacuo. The residue was dissolved in EtOAc and then poured into sat. sodium bicarb. The aqeuous layer was removed and back extracted with EtOAc. The combined organics were washed with brine, dried over sodium sulfate and concentrated to an oil. Purification on biotage again (DCM:MeOH, 0-9% B) and concentration afforded the product, I-22a, as a solid (2.207 g, 71.7%).

Workup

customSolvents were removed in vacuo
dissolutionThe residue was dissolved in EtOAc
additionpoured into sat. sodium bicarb
customThe aqeuous layer was removed
extractionback extracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated to an oil
customPurification
concentrationon biotage again (DCM:MeOH, 0-9% B) and concentration
customafforded the product, I-22a

Sources & evidence

ORD record: ord-b35b73327d2648249fc3a44cc2f0ea74
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096598B2

Reaction notes

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