1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66854680, compound

HRID 2282255Notes

Reaction equation

HRID 2282255 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]([OH:23])=O)=[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.[Cl-].[NH4+].C1C=CC2N(O)N=[N:32]C=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]([NH2:32])=[O:23])=[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

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 66855645HCID 66855645, compound

Product 1

HCID 66854680HCID 66854680, compoundYield 90.5%

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 (1.70 g, 5.0 mmol) obtained in Example 35-B(viii), TEA (2.1 mL), ammonium chloride (803 mg, 15.0 mmol), HOBT (1.01 g, 7.5 mmol), EDCI (1.44 g, 7.5 mmol) and DMF (50 mL) was stirred at rt for 16 h. The reaction mixture was concentrated under reduced pressure. To the residue was added saturated aqueous solution of sodium bicarbonate (30 mL). The resulting precipitate was collected by filtration and was washed with water and diethyl ether to give the title compound (1.54 g, 90%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added saturated aqueous solution of sodium bicarbonate (30 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwas washed with water and diethyl ether

Sources & evidence

ORD record
ord-97c75b5480214278b1888e9ee8ee7d9e
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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