Dichloromethane → HCID 67975334, compound

HRID 623906Notes

Reaction equation

C(Cl)Cl.C(O)(=O)C.[C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([CH3:32])=[CH:19][C:20]([O:23][CH2:24][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])=[N:21][CH:22]=2)=[CH:13][C:12]=1[F:33])(=[NH:10])[NH2:9].Br[CH2:35][C:36](=O)[CH2:37][CH:38]1[CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].[Na+].O>[CH:38]1([CH2:37][C:36]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[C:18]([CH3:32])=[CH:19][C:20]([O:23][CH2:24][C:25]([CH3:30])([CH3:31])[C:26]([O:28][CH3:29])=[O:27])=[N:21][CH:22]=4)=[CH:13][C:12]=3[F:33])=[N:10][CH:35]=2)[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture in which methylene chloride (10 mL) and a saturated brine (10 mL) were added to methyl 3-{[5-(4-carbamimidoyl-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate acetic acid salt (300 mg), 1-bromo-3-cyclopropylpropan-2-one (190 mg) and potassium carbonate (346 mg) was stirred at 40° C. for 5 hours. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3) to obtain methyl 3-[(5-{4-[5-(cyclopropylmethyl)-1H-imidazol-2-yl]-3-fluorophenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoate (248 mg).

Workup

customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3)

Sources & evidence

ORD record: ord-784334d397d947b4bde7dd1d0e29ee8a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302996B2

Reaction notes

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