Tetrahydrofuran → HCID 136060819, compound

HRID 1851540Notes

Reaction equation

HRID 1851540 reaction equation
[CH3:1][N:2]([S:29]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)(=[O:31])=[O:30])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH:18](C(OCC)=O)[C:19]([O:21]CC)=[O:20])[N:16]=1)=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([S:29]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:31])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[N:16]=1)=[CH:8]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 136060820HCID 136060820, compound

Product 1

HCID 136060819HCID 136060819, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of diethyl [(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-4-yl)methyl]malonate (0.43 g), 1N aqueous sodium hydroxide solution (3.2 mL), tetrahydrofuran (4 mL) and methanol (4 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated, 1N hydrochloric acid (3.2 mL) and ethylene glycol (6 mL) were added to the residue, and the mixture was stirred at 140° C. for 1 hr. Water was added to the reaction mixture and the resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (0.13 g, yield 37%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 200-201° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid (3.2 mL) and ethylene glycol (6 mL) were added to the residue
  3. stirringthe mixture was stirred at 140° C. for 1 hr
  4. additionWater was added to the reaction mixture
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3ce88efbb04943c58f05495058bd4b0d
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…