2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine → HCID 178518125, compound

HRID 706118Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH2:15])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].CS[C:24]1[NH:25][CH:26]=[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[N:34][CH:33]=2)[C:28](=[O:30])[N:29]=1>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:24]3[NH:25][CH:26]=[C:27]([CH2:31][C:32]4[CH:37]=[CH:36][N:35]=[N:34][CH:33]=4)[C:28](=[O:30])[N:29]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:18]([F:19])([F:20])[F:21]

Participants

Conditions

Temperature: 150 °C

Procedure

2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (0.317 mmol, 1.00 eq) and 2-methylsulfanyl-5-pyridazin-4-ylmethyl-1H-pyrimidin-4-one (0.341 mmol, 1.01 eq) were dissolved in dry ethanol (300 μL) and stirred at 150° C. overnight. Solvent was evaporated and crude product was purified on Biotage SP1 Snap Si 10; 15 ml/min in the gradient of MeOH in DCM: 0-7% in 15 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 2-{2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]ethylamino}-5-pyridazin-4-ylmethyl-1H-pyrimidin-4-one (0.135 mmol, yield: 43%, UPLC-MS/UV:[M+H]+=502.30; rt: 1.07 mins; purity: 95%). 1H NMR (300 MHz; CDCl3) δ/ppm 1.42 (s, 1H), 2.89 (t, J=7.33, 2H), 3.55-3.60 (m, 2H), 3.62 (s, 2H), 6.99 (dd, J=8.40, J=10.08, 2H), 7.01 (dd, J=9.07 J=3.02, 1H), 7.16-7.28 (m, 3H), 7.35-7.42 (m, 2H), 7.62-7.70 (m, 1H), 8.94 (dd, J=5.42, J=0.95, 1H), 9.09-9.12 (m, 1H)

Workup

customSolvent was evaporated
customcrude product was purified on Biotage SP1 Snap Si 10
customevaporated in vacuo

Sources & evidence

ORD record: ord-7ddf48b85848448e943945d1c7161409
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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