Hydrochloric Acid → 7-(2,3-bis(3-Fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 2276540Notes

Reaction equation

HRID 2276540 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[C:12]3=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH2:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:12]3=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66666003Ethyl 7-(2,3-bis(3-fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 566446917-(2,3-bis(3-Fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-(2,3-bis(3-fluoro-4-methylphenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (121 mg, 0.238 mmol) in THF (2 ml) and water (2 ml) was treated with LiOH (45.7 mg, 1.907 mmol) and the resulting mixture was stirred at RT for 18 h. The mixture was acidified to pH 4 with HCl and extracted with DCM. The organic extracts were combined, dried (sodium sulphate), filtered and concentrated in vacuo. The residue was azeotroped with ether to afford the title compound;

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was azeotroped with ether

Sources & evidence

ORD record
ord-8d11f728f7ea4502a8d992ed22380926
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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