Potassium Carbonate → HCID 178483268, compound

HRID 474772Notes

Reaction equation

[CH:1]([CH:3]([CH2:8][C:9]1[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=1)[C:4]([O:6]C)=O)=O.C([O-])([O-])=O.[K+].[K+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][N:37]([CH3:41])[C:38]([NH2:40])=[NH:39])=[CH:31][CH:30]=2)=[CH:24][C:23]=1[C:42]([F:45])([F:44])[F:43]>CN1C(=O)CCC1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][N:37]([CH3:41])[C:38]3[NH:40][CH:1]=[C:3]([CH2:8][C:9]4[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=4)[C:4](=[O:6])[N:39]=3)=[CH:31][CH:30]=2)=[CH:24][C:23]=1[C:42]([F:43])([F:44])[F:45]

Participants

Conditions

Temperature: 200 °C

Procedure

To the mixture of methyl 2-formyl-3-(1-methyl-1H-pyrazol-4-yl)propanoate (68.6 mg, 0.350 mmol) and K2CO3 (112 mg, 0.807 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 (35 mg, 0.055 mmol, 20.5% yield). LCMS: rt=3.00 min, [M+H+]=518.0

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-c084430f61e74c708ddae34f42137318
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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