Methanol → HCID 23582059, compound

HRID 1896540Notes

Reaction equation

HRID 1896540 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][N:3]=1.CO.[Li+].[OH-].O>C1COCC1>[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962Water2×HCID 3939Lithium HydroxideHCID 23582058HCID 23582058, compound

Product 1

HCID 23582059HCID 23582059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyl methyl 1-amino-4-(aminocarbonyl)[1]benzothieno[3,2-c]pyridine-7-carboxylate (Example 22, Step 2) dissolved in THF and MeOH was treated with a solution of LiOH in H2O (2.5 equiv). The reaction media became cloudy so H2O, MeOH and THF were added until a clear solution ensued. After 18 h, analysis showed consumption of all the starting material. A large proportion of the volatiles were removed under reduced pressure. The remaining solution was treated with 1 N HCl. The precipitate was filtered off to obtain the title compound as a solid.

Workup

  1. customThe reaction media
  2. additionwere added until a clear solution
  3. customconsumption of all the starting material
  4. customA large proportion of the volatiles were removed under reduced pressure
  5. additionThe remaining solution was treated with 1 N HCl
  6. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-ed90b757a85c4d378cfb8401a4df97ff
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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