Sodium Hydroxide → HCID 86703243, compound

HRID 2204422Notes

Reaction equation

HRID 2204422 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[N:24]([CH3:30])[CH:23]=2)[C:9]2[N:10]([CH:18]3[CH2:20][CH2:19]3)[CH:11]=[CH:12][C:13]=2[C:14]([O:16]C)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25](=[O:29])[N:24]([CH3:30])[CH:23]=2)[C:9]2[N:10]([CH:18]3[CH2:19][CH2:20]3)[CH:11]=[CH:12][C:13]=2[C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86703244HCID 86703244, compound

Product 1

HCID 86703243HCID 86703243, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 2-((4-chlorophenyl)((1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)amino)methyl)-1-cyclopropyl-1H-pyrrole-3-carboxylate (Step 240.4) (2.2 g, 5.17 mmol) and 2M NaOH (20.7 mL, 41.3 mmol) in THF (20 mL) and MeOH (20 mL) was stirred at 70° C. for 2 hr and concentrated. The aqueous residue was acidified with 2N HCl to pH 5, and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated to afford the title compound (2 g, 89% yield) as a red foam. tR: 0.94 min (LC-MS 6); ESI-MS: 412.2 [M+H]+ (LC-MS 6).

Workup

  1. concentrationconcentrated
  2. extractionextracted twice with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5bd1e48f5fe4816a1647b4b455cffce
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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