N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride → N-{4-[3-(4-t-butylbenzyl)ureidomethyl]-2-fluorophenyl}methanesulfonamide

HRID 2423351노트

반응식

HRID 2423351 반응식
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].[C:16]([C:20]1[CH:29]=[CH:28][C:23]([CH2:24][N:25]=[C:26]=[O:27])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.ClCCl>[C:16]([C:20]1[CH:29]=[CH:28][C:23]([CH2:24][NH:25][C:26](=[O:27])[NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:3]([F:2])[CH:4]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

참가 물질

5

반응물 2

HCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 220422271-Tert-butyl-4-(isocyanatomethyl)benzene

생성물 1

HCID 11625640N-{4-[3-(4-t-butylbenzyl)ureidomethyl]-2-fluorophenyl}methanesulfonamide수율 68%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

3-fluoro-4-methanesulfonylaminobenzylamine hydrochloride (1.13 g) prepared in step 3 of Example 1 was dissolved in DMF (6 mL) and diluted with dichloromethane (35 mL). To the solution were added 4-t-butylbenzylisocyanate (1.09 g) and TEA (1.2 mL) and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, diluted with ethylacetate (20 mL) and washed with water and saturated NaCl aqueous solution. The resulting solution was dried over anhydride MgSO4 and the remaining liquid was concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane/ethyl acetate=312) to yield title compound (1.23 g, 53%).

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethylacetate (20 mL)
  3. washwashed with water and saturated NaCl aqueous solution
  4. dry with materialThe resulting solution was dried over anhydride MgSO4
  5. concentrationthe remaining liquid was concentrated under reduced pressure
  6. customThe residue was purified with column chromatography (n-hexane/ethyl acetate=312)

출처 및 근거

ORD 기록
ord-4a5af75ab30f48909c6e26acbf18f74a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960584B2

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