Isopropylamine → HCID 4730718, compound

HRID 2421590Notes

Reaction equation

HRID 2421590 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>C1COCC1.CN(C=O)C>[CH:22]([NH:25][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 4730718HCID 4730718, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Oxalyl chloride (132 μL, 1.5 mmol) was added over a 10 minute period to a mixture of 3-phenylbenzoic acid (200 mg, 1 mmol) dissolved in a mixture THF/DMF (3.5 mL/58 μL). After the addition, the reaction was stirred at room temperature for 2.5 hours. Isopropylamine (511 μL, 6 mmol) was then added into the acid chloride solution at 0° C. The reaction was then stirred at room temperature for 18 hours. The reaction was concentrated and water was added to the residue. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic layers were washed with 2N HCl, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography: SiO2, CH2Cl2/AcOEt 95:5 to give a white solid (167 mg, 58%). NMR 1H (ppm, CDCl3): 7.96 (s, 1H), 7.69 (d, J3=7.68 Hz, 2H), 7.59 (d, J3=7.14 Hz, 2H), 7.50-7.33 (m, 4H), 5.93 (br. s., 1H), 4.14 (oct., J3=6.66 Hz, 1H), 1.27 (d, J=6.43 Hz, 6H).

Workup

  1. additionAfter the addition
  2. stirringThe reaction was then stirred at room temperature for 18 hours
  3. concentrationThe reaction was concentrated
  4. additionwater was added to the residue
  5. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  6. washThe combined organic layers were washed with 2N HCl, saturated NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e83ec4cd8bfd49f2a32311e24d871a18
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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