Hydrochloric Acid → HCID 59166284, compound

HRID 2188974Notes

Reaction equation

HRID 2188974 reaction equation
[F:1][C:2]1([F:37])[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]=[C:25]([C:29]6([C:32]([O:34]C)=[O:33])[CH2:31][CH2:30]6)[CH:26]=[CH:27][CH:28]=5)[C:20]([CH3:36])=[CH:19][CH:18]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.O.O[Li].O.Cl>CC(C)=O>[F:37][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]=[C:25]([C:29]6([C:32]([OH:34])=[O:33])[CH2:31][CH2:30]6)[CH:26]=[CH:27][CH:28]=5)[C:20]([CH3:36])=[CH:19][CH:18]=4)=[O:15])[CH2:12][CH2:13]3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59165848HCID 59165848, compound

Product 1

HCID 59166284HCID 59166284, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 1-(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-methylpyridin-2-yl)phenyl)cyclopropanecarboxylate (−0.26 mmol) was dissolved in acetone (3 mL) and water (3 mL) in a reaction tube. LiOH.H2O (25 mg, 60 mmol) was added, and the reaction mixture was stirred at room temperature for 16 hours. The mixture was acidified with 1N HCl until pH 1-2. The volatiles were removed under reduced pressure. The residue was taken up in methylene chloride and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The solid was triturated with Et2O, then hexanes to 1-(3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-methylpyridin-2-yl)phenyl)cyclopropanecarboxylic acid. ESI-MS m/z 493.2 (M+1)+. Retention time 1.80 minutes.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe solid was triturated with Et2O

Sources & evidence

ORD record
ord-9ac84bd5aafb4c77ba34da1572b86ead
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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