Hydrochloric Acid → 4-methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid

HRID 2070753Notes

Reaction equation

HRID 2070753 reaction equation
C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH3:41])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH2:27][CH2:28][N:29]([CH3:40])[C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH3:19])[C:12]2=[O:42])[CH:5]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:21]([O:26][CH2:27][CH3:28])[CH3:20].[CH3:7][CH2:6][CH2:5][CH:4]([CH3:9])[CH3:3].[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[CH:5][C:6]=1[N:11]1[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH3:19])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:27][CH2:28][N:29]([CH3:40])[C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[CH3:41])[C:12]1=[O:42]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 666901444-Methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid methyl ester

Product 2

HCID 21882825Ether isohexaneHCID 666896944-methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acidYield 186.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 4-Methyl-3-[3-[[1-methyl-1-[2-[2-[methyl[(phenylmethoxy)carbonyl]amino]ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzoic acid methyl ester (Example 220c, 1.97 g) in THF (11 mL) was added lithium hydroxide monohydrate (0.424 g) in water (5.5 mL) (sonicated suspension) and the reaction stirred for 16 h at room temperature. Water was added and the solution acidified with 2M hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated. Trituration with diethyl ether/iso-hexane afforded the subtitle compound (1.790 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d6b7725cc0934719852c6b00c7d12421
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

Loading…