1-methyl-1H-pyrazole-4-sulfonyl chloride → tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-({methyl[(1-methyl-1H-pyrazol-4-yl)sulfonyl]amino}methyl)phenyl]ethyl}carbamate

HRID 331694노트

반응식

HRID 331694 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH3:30])[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:31][N:32]1[CH:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[N:33]1>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:30])[S:37]([C:35]4[CH:34]=[N:33][N:32]([CH3:31])[CH:36]=4)(=[O:39])=[O:38])[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 68077950tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate

생성물 1

HCID 56835836tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-[3-({methyl[(1-methyl-1H-pyrazol-4-yl)sulfonyl]amino}methyl)phenyl]ethyl}carbamate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate (35 mg, 0.082 mmol) was dissolved in dichloromethane (0.8 mL). 4-Dimethylaminopyridine (10 mg, 0.082 mmol) and 1-methyl-1H-pyrazole-4-sulfonyl chloride (16 mg, 0.09 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with ethyl acetate (20 ml) and washed with aqueous hydrochloric acid (1 N, 5 ml, twice) and sodium bicarbonate. The organic layer was dried (magnesium sulfate) and concentrated in vacuo. The crude product was purified by preparative thin layer chromatography (silica, ethyl acetate, n-heptane). Yield: 36 mg (0.063 mmol, 77%)

후처리

  1. washwashed with aqueous hydrochloric acid (1 N, 5 ml
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative thin layer chromatography (silica, ethyl acetate, n-heptane)

출처 및 근거

ORD 기록
ord-139465d4a1ca4c4789850d68311ff3be
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877794B2

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