Hydrochloric Acid → HCID 66689941, compound

HRID 337136Notes

Reaction equation

HRID 337136 reaction equation
O.[OH-].[Li+].[Cl:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([NH:17][C:18]1[C:19](=[O:36])[N:20]([C:24]2[CH:25]=[C:26]([CH:31]=[C:32]([F:35])[C:33]=2[CH3:34])[C:27]([O:29]C)=[O:28])[CH:21]=[CH:22][N:23]=1)([CH3:16])[CH3:15].Cl>O.C1COCC1>[Cl:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([NH:17][C:18]1[C:19](=[O:36])[N:20]([C:24]2[CH:25]=[C:26]([CH:31]=[C:32]([F:35])[C:33]=2[CH3:34])[C:27]([OH:29])=[O:28])[CH:21]=[CH:22][N:23]=1)([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66688914HCID 66688914, compound

Product 1

HCID 66689941HCID 66689941, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.177 g) in water (5.00 mL) was added to methyl 3-[3-({1-[2-(2-chloroethoxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-5-fluoro-4-methylbenzoate (Example 316b, 1.17 g) in THF (10 mL) and the reaction mixture was stirred for 4 h at room temperature. Water was added and the solution acidified with 2M HCl. This was extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and evaporated to afford the subtitle compound as a solid (1 g).

Workup

  1. extractionThis was extracted into ethyl acetate (2×)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3c74b984d42449a4bef0539ce86dbed4
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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