Triethylamine → N-Methanesulfonyl-N1-[4-(2-benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine

HRID 626070ノート

反応式

HRID 626070 の反応式
[CH2:1]([O:8][C:9]1[CH:27]=[C:26]([CH2:28][CH3:29])[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][NH2:22])=[CH:14][C:13]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:37](Cl)([CH3:40])(=[O:39])=[O:38]>ClCCl>[CH3:40][S:37]([N:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]2[CH:24]=[CH:25][C:26]([CH2:28][CH3:29])=[CH:27][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:13]([F:23])[CH:14]=1)[CH2:19][CH2:20][CH2:21][NH2:22])(=[O:39])=[O:38]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59191220N1-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine

生成物 1

HCID 68549012N-Methanesulfonyl-N1-[4-(2-benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine収率 82.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N1-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine (90 mg, 0.23 mmol) in 5 ml of dry dichloromethane and 0.08 ml (0.57 mmol) of triethylamine, cooled to 0° C., was added mesyl chloride (26 mg, 0.23 mmol) taken in 0.5 ml of dichloromethane dropwise. The reaction was quenched after 5 minutes as the reaction was complete on TLC. The reaction mixture was diluted with water and the layers separated. The aqueous layer was extracted with dichloromethane and the combined dichloromethane fraction was washed with water, dried over anhydrous Na2SO4 and concentrated. The crude residue obtained was combined with the crude obtained from an earlier 20 mg batch and column purified over silica gel using 2% methanol in dichloromethane as eluant to get 90 mg, 68.3% of title compound.

後処理

  1. customThe reaction was quenched after 5 minutes as the reaction
  2. additionThe reaction mixture was diluted with water
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washthe combined dichloromethane fraction was washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe crude residue obtained
  9. customobtained from an earlier 20 mg batch and column
  10. custompurified over silica gel using 2% methanol in dichloromethane as eluant

出典と根拠

ORDレコード
ord-215732276e9b41c8a836728aa4a70f98
出典データセット
uspto-grants-2016_04
特許番号
US09309179B2

反応ノート

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