1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58545553, compound

HRID 71991Notes

Reaction equation

HRID 71991 reaction equation
[S:1]1[C:5]([C:6](O)=[O:7])=[CH:4][CH:3]2[S:9][CH:10]=[CH:11][CH:2]12.C1C=C[C:15]2[N:20]([OH:21])N=NC=2C=1.[CH3:22]CN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH3:22][O:21][N:20]([CH3:15])[C:6]([C:5]1[S:1][CH:2]2[CH:11]=[CH:10][S:9][CH:3]2[CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 600973103a,6a-Dihydrothieno[3,2-b]thiophene-2-carboxylic acid

Product 1

HCID 58545553HCID 58545553, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3a,6a-Dihydro-thieno[3,2-b]thiophene-2-carboxylic acid (2 g, 10.86 mmol) MeNHOMe—HCl (1.06 g, 10.86 mmol), HOBt (1.47 g, 10.86 mmol) and DIPEA (5.9 mL, 33.67 mmol) were combined in DMF (40 mL). To the stirred mixture was added EDCI (2.72 g, 14.12 mmol). After 5 h, EtOAc (100 mL) was added and the organics were washed with saturated aqueous NaHCO3 and brine then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 45% EtOAc/Hex) to afford the title compound (1.98 g, 80%).

Workup

  1. washthe organics were washed with saturated aqueous NaHCO3 and brine
  2. dry with materialthen dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica column chromatography (20% to 45% EtOAc/Hex)

Sources & evidence

ORD record
ord-fc7dd58f56e440a59f723ee38adabebc
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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