2-Bromo-1-(2-chloro-4-methoxy-5-methylphenyl)-1-propanone → HCID 10180607, compound

HRID 1178556Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]1.Br[CH:16]([CH3:29])[C:17]([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH3:27])=[CH:21][C:20]=1[Cl:28])=O>CN(C=O)C>[Cl:28][C:20]1[CH:21]=[C:22]([O:26][CH3:27])[C:23]([CH3:25])=[CH:24][C:19]=1[C:17]1[N:14]=[C:12]([C:9]2([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH2:11][CH2:10]2)[O:13][C:16]=1[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2,4-Dichloro-phenyl)-cyclopropanecarboxylic acid amide (46 mg, 0.2 mmol) and 2-Bromo-1-(2-chloro-4-methoxy-5-methly-phenyl)-propan-1-one (58 mg, 0.2 mmol) were combined in DMF (1 mL) at 0.2 M and the mixture heated to 80° C. overnight. The reaction was then cooled to room temperature. The desired product was purified by reversed phase HPLC/MS using an acetonitrile/water gradient and C18 stationary phase. Yield: 1 mg (2%) [MH]+ 424.2, 422.2, 426.0 (small).

Workup

temperatureThe reaction was then cooled to room temperature
customThe desired product was purified by reversed phase HPLC/MS

Sources & evidence

ORD record: ord-dc122090ccea4b80bd93fa67e8d2a27b
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276526B2

Reaction notes

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