1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58504347, compound

HRID 1941893Notes

Reaction equation

HRID 1941893 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.O[NH:38][C:39](=[NH:48])[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=1>CN(C=O)C.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:13]1[O:15][N:48]=[C:39]([C:40]2[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][CH:41]=2)[N:38]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7468145-Amino-1-phenyl-1H-pyrazole-4-carboxylic acidHCID 178513316HCID 178513316, compound

Product 1

HCID 58504347HCID 58504347, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Amino-1-phenyl-1H-pyrazole-4-carboxylic acid (1.8 g, 8.86 mmol), HOBt (1.357 g, 8.86 mmol) and EDCI (1.698 g, 8.86 mmol) were dissolved in DMF (12 mL) under nitrogen at room temperature. The resulting clear, pale yellow solution was stirred for 30 minutes then N-hydroxy-4-(hydroxymethyl)benzimidamide (1.472 g, 8.86 mmol) was added in several portions. The reaction was placed in an oil bath set to 130° C. After 4 hours, the solution was cooled to RT and then added to rapidly stirring water (50 mL). The initial precipitate was stirred and sonicated to give a yellow solid which was collected by filtration, washed with water, air dried and then dried under vacuum to afford (4-(5-(5-amino-1-phenyl-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (1.5 g 4.05 mmol).

Workup

  1. customThe reaction was placed in an oil bath
  2. customset to 130° C
  3. waitAfter 4 hours
  4. customsonicated
  5. customto give a yellow solid which
  6. filtrationwas collected by filtration
  7. washwashed with water, air
  8. customdried
  9. customdried under vacuum

Sources & evidence

ORD record
ord-c8fd66aa1a3f4f26b7971f4acfe6b4d4
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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