Ethyl chloroformate → HCID 68826227, compound

HRID 1723920Notes

Reaction equation

HRID 1723920 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:12][C:11]2[C:10]([NH2:13])=[N:9][NH:8][C:7]=2[CH:6]=1)=[O:4].CCN(C(C)C)C(C)C.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1>[NH2:13][C:10]1[C:11]2[S:12][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=2[N:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:9]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 44558323Methyl 3-amino-1H-thieno[3,2-c]pyrazole-5-carboxylate

Product 1

HCID 68826227HCID 68826227, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled suspension of 3-amino-1H-thieno[3,2-c]pyrazole-5-carboxylic acid methyl ester (35.5 mmol, 7.0 g) and N,N′-diisopropylethylamine (0.21 mol, 36.5 mL) in 71 mL of tetrahydrofuran were added, dropwise, 3.5 mL of ethyl chloroformate (36.6 mmol). After 1.5 hours, the cold suspension was concentrated under vacuum and diluted with dichloromethane. The organic phase was washed with buffer pH 4, sodium hydroxide 1 N, brine and dried over Na2SO4. The filtrate was evaporated to dryness and triturated with dichloromethane to give 6 g 1-ethyl 5-methyl 3-amino-1H-thieno[3,2-c]pyrazole-1,5-dicarboxylate (7)

Workup

  1. additionwere added
  2. concentrationthe cold suspension was concentrated under vacuum
  3. additiondiluted with dichloromethane
  4. washThe organic phase was washed with buffer pH 4, sodium hydroxide 1 N, brine
  5. dry with materialdried over Na2SO4
  6. customThe filtrate was evaporated to dryness
  7. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-3cef6e1b89e84ee2a2f70ffce59019f5
Source dataset
uspto-grants-2009_02
Patent number
US07485661B2

Reaction notes

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