Hydrochloric Acid → HCID 71657645, compound

HRID 517889Notes

Reaction equation

HRID 517889 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[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]2=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22].[Li+].[OH-].O.Cl>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[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]2=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 89690069HCID 89690069, compound

Product 1

HCID 71657645HCID 71657645, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-(2,3-bis(2,4-difluorophenyl)-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (480 mg, 0.931 mmol) in THF (2.5 ml) was treated with LiOH (178 mg, 7.45 mmol) followed by water (2.5 ml) and stirred vigorously for 3 days. The mixture was acidified to pH4/5 using 5M HCl and extracted with DCM. The combined organic extracts were dried (sodium sulphate), filtered and concentrated under reduced pressure. Purification was carried out on silica eluting with 20-25% TBME in DCM. The resulting product was further purified under the following conditions to afford the titled compound;

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (sodium sulphate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. customThe resulting product was further purified under the following conditions

Sources & evidence

ORD record
ord-cef5015fac884649afad84d51e706131
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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