Water → HCID 136011087, compound

HRID 453592Notes

Reaction equation

HRID 453592 reaction equation
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]3[S:14][C:13]([C:15](OCC)=[O:16])=[N:12][N:11]=3)[NH:5][C:4]=2[C:3]=1[N:20]([CH3:29])[S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:16][CH2:15][C:13]1[S:14][C:10]([C:6]2[NH:5][C:4]3[C:3]([N:20]([CH3:29])[S:21]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)(=[O:22])=[O:23])=[C:2]([CH3:1])[S:9][C:8]=3[CH:7]=2)=[N:11][N:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 136011086HCID 136011086, compound

Product 1

HCID 136011087HCID 136011087, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-{2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrol-5-yl}-1,3,4-thiadiazole-2-carboxylate (1.3 g) in tetrahydrofuran (20 mL) was slowly added lithium aluminum hydride (114 mg) in small portions. The mixture was stirred at room temperature for 1 hr, and water (0.15 mL), 15% aqueous sodium hydroxide solution (0.15 mL) and water (0.45 mL) were successively added to the reaction mixture under ice-cooling. The mixture was stirred for 1 hr, and the insoluble material was filtered off. The filtrate was concentrated and crystallized from diethyl ether to give N-{5-[5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl]-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl}-N-methylthiophene-2-sulfonamide (370 mg, yield 31%) as brown crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hr
  3. filtrationthe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-55890f7500bf4c8ab425efb2cb96ccab
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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