Triethylamine → HCID 90390115, 화합물

HRID 59780노트

반응식

HRID 59780 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 90390115HCID 90390115, 화합물수율 68.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e174cbba3c914527813baec7300f01fb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440941B2

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