Dimethyl Sulfoxide → Biphenyl-2-ylcarbamic Acid 1-[2-(4-Formylphenylcarbamoyl)ethyl]piperidin-4-yl Ester

HRID 907637노트

반응식

HRID 907637 반응식
N[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21](=[O:35])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:16][CH2:15]2)=[O:11])=[CH:5][CH:4]=1.NC1C=CC(C[OH:42])=CC=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CS(C)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21](=[O:35])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:16][CH2:15]2)=[O:11])=[CH:5][CH:4]=1)=[O:42]

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 693314-Aminobenzyl alcoholHCID 81531Diisopropylethylamine2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59340340Biphenyl-2-ylcarbamic Acid 1-[2-(4-Aminomethylphenylcarbamoyl)ethyl]piperidin-4-yl Ester

생성물 1

HCID 59340337Biphenyl-2-ylcarbamic Acid 1-[2-(4-Formylphenylcarbamoyl)ethyl]piperidin-4-yl Ester수율 66%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of biphenyl-2-ylcarbamic acid 1-[2-(4-aminomethylphenylcarbamoyl)ethyl]piperidin-4-yl ester (1 g, 2.7 mmol; prepared as described in Preparation 14), 4-aminobenzyl alcohol (498 mg, 4.05 mmol), HATU (1.54 g, 4.05 mmol) and DIPEA (1.41 mL, 8.1 mmol) in DCM (14 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with 100 mL of DCM and washed first with a 1:3 mixture of 1N HCl/water (100 mL), then brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was dissolved in DCM (100 mL) and the solution was cooled to −5° C. DIPEA (1.1 mL, 6.33 mmol) and DMSO (1.5 mL, 21.1 mmol) were added to the solution, followed by sulfur trioxide pyridine complex (1 g, 6.33 mmol). The reaction mixture was stirred at 0° C. for 1 hour then washed with a saturated solution of sodium bicarbonate (100 mL) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated to give 0.84 g of the title intermediate (66% yield) as an oil.

후처리

  1. washwashed first with a 1:3 mixture of 1N HCl/water (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in DCM (100 mL)
  6. temperaturethe solution was cooled to −5° C
  7. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  8. washthen washed with a saturated solution of sodium bicarbonate (100 mL) and brine (100 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-06e5cd2317dd40afa7fa3961aaafc8b3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013152B2

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