HCID 68739627, compound → HCID 68741580, compound

HRID 869912Notes

Reaction equation

[F:1][C:2]1([F:32])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[N:22]=[C:21]([C:23]5[C:24]([O:29]C)=[N:25][CH:26]=[CH:27][CH:28]=5)[C:20]([CH3:31])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1>O1CCOCC1.Cl>[F:32][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:31])=[C:21]([C:23]5[C:24](=[O:29])[NH:25][CH:26]=[CH:27][CH:28]=5)[N:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(2′-methoxy-3-methyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (66 mg, 0.15 mmol) was dissolved in a mixture of 1 mL of 1,4-dioxane and 0.5 mL of 4M aqueous hydrochloric acid. This solution was heated at 90° C. for 3 hours. The crude product was then purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(2-oxo-1,2-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide. ESI-MS m/z calc. 425.1. found 426.0 (M+1)+. Retention time 1.33 minutes.

Workup

customThe crude product was then purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record: ord-93ec2bb183f54353ad472dac00f9e599
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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