1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86649609, compound

HRID 1530091Notes

Reaction equation

HRID 1530091 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21](O)=[O:22])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1.C1C=C[C:27]2[N:32]([OH:33])N=NC=2C=1.[CH3:34]CN=C=NCCCN(C)C>CN(C=O)C>[CH3:34][O:33][N:32]([CH3:27])[C:21]([C:12]1[S:11][C:10]([C:9]2[C:2]([CH3:1])=[N:3][N:4]3[CH:8]=[CH:7][S:6][C:5]=23)=[N:14][C:13]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:22]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66855645HCID 66855645, compound

Product 1

HCID 86649609HCID 86649609, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazole-5-carboxylic acid (1.53 g, 4.5 mmol) obtained in Example 35-B(viii), TEA (1.9 mL), N,O-dimethylamine hydrochloride (1.32 g, 13.5 mmol), HOBT (912 mg, 6.75 mmol), EDCI (1.30 g, 6.75 mmol) and DMF (45 mL) was stirred at rt for 16 h. The reaction mixture was concentrated under reduced pressure, and water (50 mL) was added to the reaction mixture. The aqueous layer was extracted with EtOAc (50 mL×2), and the combined organic layer was washed with saturated aqueous solution of sodium bicarbonate (50 mL) and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0) to give the title compound (1.43 g, 83%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (50 mL)
  2. additionwas added to the reaction mixture
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  4. washthe combined organic layer was washed with saturated aqueous solution of sodium bicarbonate (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customInsoluble materials were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→100/0)

Sources & evidence

ORD record
ord-b1da6eec8b114da09031e2e9994078a0
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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