N-[2-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-N-methylguanidine → HCID 178494133, compound

HRID 706009Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([CH3:21])[C:18]([NH2:20])=[NH:19])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].[CH:26]([CH:28]([CH2:33][C:34]1[CH:35]=[N:36][C:37]([O:40][CH3:41])=[N:38][CH:39]=1)[C:29](OC)=O)=[O:27]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([CH3:21])[C:18]3[NH:20][CH:29]=[C:28]([CH2:33][C:34]4[CH:35]=[N:36][C:37]([O:40][CH3:41])=[N:38][CH:39]=4)[C:26](=[O:27])[N:19]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:22]([F:23])([F:24])[F:25]

Participants

Conditions

Temperature: 200 °C

Procedure

To the solution of N-[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-N-methylguanidine (100 mg, 0.269 mmol), methyl 2-formyl-3-[2-(methyloxy)-5-pyrimidinyl]propanoate (78 mg, 0.350 mmol) in NMP (5 mL) was added neat N-[2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl]-N-methylguanidine (100 mg, 0.269 mmol). The reaction mixture was heated with a microwave reactor at 200° C. for 2 h. Purification via MDAP then afforded the title compound as a white solid (33 mg, 0.050 mmol, 18.5% yield). LCMS: rt=3.14 min, [M+H+]=545.9

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-f2dfd88353aa456e82b5d701283c32c2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

Loading…