Lithium Hydroxide → 2-(5-(6-(1-(2,2-difluorobenzo[d][1,3]-dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)acetic acid

HRID 869977Notes

Reaction equation

[F:1][C:2]1([F:36])[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[CH:24]=[CH:25][C:26](=[O:34])[N:27]([CH2:29][C:30]([O:32]C)=[O:31])[CH:28]=5)[C:20]([CH3:35])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[OH-].[Li+]>O1CCOCC1>[F:36][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[N:22]=[C:21]([C:23]5[CH:24]=[CH:25][C:26](=[O:34])[N:27]([CH2:29][C:30]([OH:32])=[O:31])[CH:28]=5)[C:20]([CH3:35])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a flask containing methyl 2-(5-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)acetate (0.13 g, 0.27 mmol) was added a mixture of 2M Lithium hydroxide (1 mL of 2 M, 2.0 mmol) and 1,4-dioxane (4 mL) and the reaction mixture was heated to 60° C. for 2 hrs. The reaction mixture was evaporated and the resulting residue was suspended between ethyl acetate (10 mL) and 1N hydrochloric acid (10 mL). The organics were dried over sodium sulfate and evaporated to give the product (0.13 g, 98%). ESI-MS m/z calc. 483.12. found 484.5 (M+1)+ Retention time 1.59 minutes.

Workup

additionwas added
customThe reaction mixture was evaporated
dry with materialThe organics were dried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-b982f051b52c47bc9c531f812bdc6fa6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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