Sodium hydride → HCID 11778364, compound

HRID 1063110Notes

Reaction equation

HRID 1063110 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([SH:14])[C:8]=1[C:15]#[N:16])[CH3:4].Br[CH2:19][C:20]([NH2:22])=[O:21]>C1COCC1.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[CH2:3]([O:5][C:6]([C:7]1[C:8]2[C:15]([NH2:16])=[C:19]([C:20](=[O:21])[NH2:22])[S:14][C:9]=2[N:10]=[C:11]([CH3:13])[CH:12]=1)=[O:17])[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 696322-BromoacetamideHCID 178469058HCID 178469058, compound

Product 1

HCID 11778364HCID 11778364, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

NaH (39 mg, 0.95 mmol) was added to a solution of the above ester (210 mg, 0.95 mmol) in THF (15 mL) at room temperature. After stirring for 5 min, α-bromoacetamide (134 mg, 0.97 mmol) and n-Bu4NI (10 mg) were added. The mixture was stirred at room temperature for 1 h, then NaH (39 mg, 0.95 mmol) was added, and the mixture was stirred for an additional 0.5 h. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated giving an orange solid. The crude residue was recrystallized from MeOH giving 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid ethyl ester (160 mg, 60%), m.p. 205-208° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. stirringthe mixture was stirred for an additional 0.5 h
  3. customThe reaction was quenched by addition of saturated aqueous NH4Cl
  4. additiondiluted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customgiving an orange solid
  9. customThe crude residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-109399d007794ff6bd3b85e061115394
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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