Methanol → HCID 22603639, compound

HRID 2308104Notes

Reaction equation

HRID 2308104 reaction equation
C1COCC1.CO.O[Li].O.C[O:12][C:13]([C:15]1[S:23][C:22]2[C:17](=[N:18][CH:19]=[CH:20][C:21]=2[O:24][C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([C:34](=[O:37])[NH:35][CH3:36])[C:29]([CH3:38])=[CH:28]3)[CH:16]=1)=[O:14]>O>[CH3:38][C:29]1[N:30]([C:34](=[O:37])[NH:35][CH3:36])[C:31]2[C:27]([CH:28]=1)=[CH:26][C:25]([O:24][C:21]1[CH:20]=[CH:19][N:18]=[C:17]3[CH:16]=[C:15]([C:13]([OH:14])=[O:12])[S:23][C:22]=13)=[CH:33][CH:32]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 20746072HCID 20746072, compound

Product 1

HCID 22603639HCID 22603639, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of THF (5 mL), MeOH (1 mL) and H2O (1 mL) was used to dissolve LiOH.H2O (0.042 g, 1.0 mmol) and then added 7-(2-Methyl-1-methylcarbamoyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid methyl ester (0.35 g, 0.89 mmol) added. The solution was stirred at 25° C. for 2 h, quenched with several drops of 1N HCl then concentrated. The precipitate was rinsed with H2O (2×5 mL) and Et2O (2×5 mL), dried under high vacuum for 2 h and used as is to afford 7-(2-Methyl-1-methylcarbamoyl-1H-indol-5-yloxy)-thieno[3,2-b]pyridine-2-carboxylic acid (0.25 g, 73%) as yellow solid. HPLC: Rt 3.43 min. (95% area). LCMS (ACPI) M+H+ m/z: 382.1.

Workup

  1. customquenched with several drops of 1N HCl
  2. concentrationthen concentrated
  3. washThe precipitate was rinsed with H2O (2×5 mL) and Et2O (2×5 mL)
  4. customdried under high vacuum for 2 h

Sources & evidence

ORD record
ord-7c575b1a318642ea83de4a96a512547a
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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