Diisopropylcarbodiimide → HCID 68715436, compound

HRID 1873766Notes

Reaction equation

HRID 1873766 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:22]=C=NC(C)C)(C)C.N1(O)C2C=CC=CC=2N=N1>CN(C=O)C>[O:1]([C:8]1[N:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([NH2:22])=[O:18])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 757711-Hydroxybenzotriazole2×HCID 27977433-(6-Phenoxypyridin-3-yl)prop-2-enoic acid

Product 1

HCID 68715436HCID 68715436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.415 mmol) of 3-(6-phenoxy-pyridin-3-yl)-acrylic acid was dissolved in 4 ml of DMF, and 52 mg (0.415 mmol) of N,N′-diisopropylcarbodiimide and 126 mg (0.830 mmol) of the ammonium salt of benzotriazol-1-ol were added. After 1 h a further 126 mg (0.830 mmol) of the ammonium salt of benzotriazol-1-ol were added. The reaction was stirred at room temperature for 16 h, filtered, and the product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization, the product was obtained as a solid. Yield: 75 mg.

Workup

  1. filtrationfiltered
  2. customthe product was purified by preparative RP HPLC
  3. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
  4. customAfter lyophilization, the product was obtained as a solid

Sources & evidence

ORD record
ord-014ae29b36054fd9bc21c45f30029db1
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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