Triethylamine → HCID 178522641, compound

HRID 869646Notes

Reaction equation

HRID 869646 reaction equation
[F:1][C:2]([F:28])([F:27])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][O:17][C:18]2[C:19]([C:24](O)=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:10])[CH2:5][CH2:4]1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[N:42]1[N:43]=[C:44]([NH2:47])[NH:45][CH:46]=1>ClCCl.CN(C)C=O>[N:42]1[N:43]=[C:44]([NH:47][C:24](=[O:25])[C:19]2[C:18]([O:17][CH2:16][C@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([C@H:6]3[CH2:5][CH2:4][C@H:3]([C:2]([F:27])([F:1])[F:28])[CH2:8][CH2:7]3)=[O:10])=[CH:23][CH:22]=[CH:21][N:20]=2)[NH:45][CH:46]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178509196HCID 178509196, compoundHCID 178524885HCID 178524885, compound

Product 1

HCID 178522641HCID 178522641, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid (30 mg, 0.08 mmol, EXAMPLE 34 Step 3) in dichloromethane (1 mL) were added oxalyl chloride (33 microL, 0.38 mmol) and a catalytic amount of N,N-dimethylformamide at room temperature. After being stirred at room temperature for 30 min, the volatile was removed under reduced pressure. The resulting residue was dissolved in toluene (1 mL). Triethyl amine (10 microL, 0.08 mmol) and 4H-1,2,4-triazol-3-amine (8 mg, 0.09 mmol) were added to the mixture. After being refluxed for 15 h, the volatile was removed by evaporation. The residual material was dissolved in dichloromethane. The organic layer was washed with aq. sodium bicarbonate and concentrated in vacuo to afford the title compound as a brown oil. The crude product was purified by preparative HPLC.

Workup

  1. customat room temperature
  2. customthe volatile was removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in toluene (1 mL)
  4. temperatureAfter being refluxed for 15 h
  5. customthe volatile was removed by evaporation
  6. dissolutionThe residual material was dissolved in dichloromethane
  7. washThe organic layer was washed with aq. sodium bicarbonate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cf920f3649b4fdf8cf3790581242fc6
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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