Hydrochloric Acid → 4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-2-fluorobenzoic acid

HRID 1946807Notes

Reaction equation

HRID 1946807 reaction equation
[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[C:19]([F:27])[CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]1([N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[C:19]([F:27])[CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25183072HCID 25183072, compound2×

Product 1

HCID 594470154-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]-2-fluorobenzoate (Intermediate 25, 85 mg; 0.20 mmol) in THF (5 ml) and MeOH (5 ml) was treated with an aqueous solution (5 M) of sodium hydroxide (198 μl; 0.99 mmol). After stirring for 40 hours, HCl 1 N was added until pH 3, then the solution was concentrated under vacuum, AcOEt was added and the organic layer was washed with brine, dried (MgSO4) and removed under vacuum to afford an oily residue which was purified by preparative HPLC to give the title compound as an amorphous white solid.

Workup

  1. concentrationthe solution was concentrated under vacuum, AcOEt
  2. additionwas added
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customremoved under vacuum
  6. customto afford an oily residue which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-a61d4209b8394dbb89607e7086c56384
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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