4-Methylmorpholine → N-[2-(2,3-Dimethylphenoxy)-1-methylethyl)-N-methyl-2-(4-methanesulfonamido-phenyl)-acetamide

HRID 1386475노트

반응식

HRID 1386475 반응식
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:31][NH:32][CH:33]([CH3:44])[CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[C:37]=1[CH3:43]>CN(C)C=O.C(N(CC)CC)C>[CH3:43][C:37]1[C:38]([CH3:42])=[CH:39][CH:40]=[CH:41][C:36]=1[O:35][CH2:34][CH:33]([N:32]([CH3:31])[C:13](=[O:15])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=1)[CH3:44]

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 27738874-(Methylsulphonylamino)phenylacetic acidHCID 21182036N-methyl-2-(2,3-dimethylphenoxy)-1-methylethylamine

생성물 1

HCID 21182026N-[2-(2,3-Dimethylphenoxy)-1-methylethyl)-N-methyl-2-(4-methanesulfonamido-phenyl)-acetamide수율 80%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매

반응 조건

온도
-10 °C

실험 절차

To a solution containing 0.80 g (3.5 mmol) of 4-methanesulfonamido-phenylacetic acid (Example 32) in 20 ml of N,N-dimethylformamide (DMF) 0.46 ml (0.42 g, 4,2 mmol) of 4-methylmorpholine is added, the mixture is cooled to −10° C. and 0.65 ml (0.70 g, 5 mmol) of isobutyl chloroformate is added. After 10 minutes a solution containing 0.68 g (3.5 mmol) of N-methyl-2-(2,3-dimethylphenoxy)-1-methylethylamine (Example 44) in 3 ml of DMF pre-cooled to −10° C. is added, then the pH value of the mixture is adjusted to 8.5 by adding triethylamine. The reaction mixture is stirred at −10° C. for 1 hour, then at 0° C. for 1 hour. Then, the solvent is evaporated under reduced pressure and the solid residue is alkalinized by adding aqueous ammonia solution and distributed between water and ethyl acetate. The aqueous phase is washed twice with ethyl acetate, the combined organic phase is washed once with water, dried over sodium sulphate and evaporated. Thus, 1.13 g of the title substance are obtained as an amorphous substance, which is suitable to the next step without further purification. Yield: 80%.

후처리

  1. additionis added
  2. temperaturepre-cooled to −10° C.
  3. additionis added
  4. waitat 0° C. for 1 hour
  5. customThen, the solvent is evaporated under reduced pressure
  6. additionby adding aqueous ammonia solution
  7. washThe aqueous phase is washed twice with ethyl acetate
  8. washthe combined organic phase is washed once with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated
  11. customThus, 1.13 g of the title substance are obtained as an amorphous substance, which
  12. customis suitable to the next step without further purification

출처 및 근거

ORD 기록
ord-a883dd220fbf468a82b9a09bd71b29d4
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265445B1

반응 노트

불러오는 중…