Lithium Hydroxide → 6-(1-(2,2-Difluorobenzo[d][1,3]-dioxol-5-yl)cyclopropanecarboxamido)-6'-methoxy-3-methyl-2,3'-bipyridine-5'-carboxylic acid

HRID 869974Notes

Reaction equation

HRID 869974 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]=[N:25][C:26]([O:33][CH3:34])=[C:27]([C:29]([O:31]C)=[O:30])[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]=[N:25][C:26]([O:33][CH3:34])=[C:27]([C:29]([OH:31])=[O:30])[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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71053039Methyl 6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-6'-methoxy-3-methyl-2,3'-bipyridine-5'-carboxylate

Product 1

HCID 710530426-(1-(2,2-Difluorobenzo[d][1,3]-dioxol-5-yl)cyclopropanecarboxamido)-6'-methoxy-3-methyl-2,3'-bipyridine-5'-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flask containing methyl 6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-6′-methoxy-3-methyl-2,3′-bipyridine-5′-carboxylate (0.22 g, 0.45 mmol) was added a mixture of 2M Lithium hydroxide (2.5 mL of 2 M, 5.0 mmol) and 1,4-dioxane (2.5 mL) and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was evaporated and residue was suspended between dichloromethane (10 mL) and 1N hydrochloric acid (10 mL). The organics were dried over sodium sulfate and evaporated to give the product (0.20 g, 95%). ESI-MS m/z calc. 483.12. found 484.5 (M+1)+ Retention time 1.85 minutes.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. dry with materialThe organics were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-bdc1c353688349708a582a5ab27c6c79
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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