Triethylamine → HCID 69099565、化合物

HRID 2251542ノート

反応式

HRID 2251542 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.CCN(CC)CC.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH3:23][C:16]([O:15][C:14]1[CH:24]=[CH:25][C:11]([CH2:10][CH2:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:45]([CH3:44])(=[O:47])=[O:46])=[CH:7][N:6]=2)[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)=[CH:12][CH:13]=1)([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:44][S:45]([N:1]([S:45]([CH3:44])(=[O:47])=[O:46])[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:22])([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1)(=[O:47])=[O:46]

参加物

6

反応物 3

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chloride2 回HCID 59643282HCID 59643282、化合物

生成物 2

HCID 69099565HCID 69099565、化合物収率 46%HCID 69099627HCID 69099627、化合物収率 13%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 2-[4-(2-{(5-aminopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (65 mg; 0.13 mmol) in 3 ml of dichloromethane was treated with Et3N (0.019 ml; 0.14 mmol) and methanesulfonyl chloride (0.011 ml; 0.14 mmol). After 30 minutes, additional amounts of Et3N (0.019 ml) and methanesulfonyl chloride (0.011 ml) were added and stirred for another 30 minutes. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl and brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (10–70%) provided two main products: ethyl 2-methyl-2-[4-(2-{{5-[(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (10 mg; 13% yield; MS: m/z 580 (M+1)) and ethyl 2-[4-(2-{{5-[bis(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (39 mg; 46% yield; MS: m/z 658 (M+1)). (Both of these products can be hydrolyzed to the title compound).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and 0.5N HCl
  3. washThe organic phase was washed with 0.5N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by radial chromatography
  7. customprovided two main products

出典と根拠

ORDレコード
ord-49a2d321025c4fe2a28254510f0a4098
出典データセット
uspto-grants-2008_01
特許番号
US07319104B2

反応ノート

読み込み中…