Triethylamine → HCID 90390115, compound

HRID 59780Notes

Reaction equation

HRID 59780 reaction equation
[F:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[C:25]1([CH:31]2[CH2:40][CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:41][CH:42]4[CH2:47][CH2:46][CH:45](O)[CH2:44][CH2:43]4)[CH:37]=3)[O:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:25]1([CH:31]2[CH2:40][CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([O:41][CH:42]4[CH2:47][CH2:46][CH:45]([O:5][C:4](=[O:6])[C:3]5[CH:7]=[CH:8][N:9]=[CH:10][C:2]=5[F:1])[CH2:44][CH2:43]4)[CH:37]=3)[O:32]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 903899804-(2-Phenyl-chroman-6-yloxy)-cyclohexanol

Product 1

HCID 90390115HCID 90390115, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 158 mg of 3-fluoroisonicotinic acid (1.12 mmol) and 156 μl of triethylamine (1.12 mmol) in 16 ml of dichloromethane at 15° C. 138 μl of pivaloyl chloride (1.12 mmol) were added dropwise. The solution was stirred for 30 min. A solution of 110 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanol (0.34 mmol) in 4 ml of dichloromethane was added and 82 mg of 4-dimethylamino-pyridine (0.68 mmol) were added in one portion. Stirring at room temperature was continued for 16 h. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and filtered, and the solvent removed by evaporation. The resulting oil was purified by reversed phase HPLC. 104 mg of the title compound were isolated as solid (69%).

Workup

  1. customat 15° C
  2. stirringStirring at room temperature
  3. waitwas continued for 16 h
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
  5. extractionthe aqueous layer extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed by evaporation
  9. customThe resulting oil was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-e174cbba3c914527813baec7300f01fb
Source dataset
uspto-grants-2016_09
Patent number
US09440941B2

Reaction notes

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