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

HRID 2423351ノート

反応式

HRID 2423351 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4a5af75ab30f48909c6e26acbf18f74a
出典データセット
uspto-grants-2011_06
特許番号
US07960584B2

反応ノート

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