Triethylamine → 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3'-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamide

HRID 1428730ノート

反応式

HRID 1428730 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH3:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=2[CH2:36][NH2:37])[CH:23]=[CH:24][CH:25]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([NH:37][CH2:36][C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:33])([F:34])[F:35])=[CH:31][C:26]=2[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=2)=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680213(3'-Methyl-5-(trifluoromethyl)biphenyl-2-yl)methanamine

生成物 1

HCID 715396382-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3'-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamide収率 84%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (51 mg, 0.185 mmol) and (3′-methyl-5-(trifluoromethyl)biphenyl-2-yl)methanamine (60 mg, 0.222 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (53 mg, 0.2775 mmol), 1-hydroxybenzotriazole (38 mg, 0.270 mmol) and triethylamine (0.06 mL, 0.4625 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3′-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamide (example 22) (81 mg) was obtained as 84% yield.

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-ee0b477a96074bda986a75a353b6e6df
出典データセット
uspto-grants-2015_01
特許番号
US08937092B2

反応ノート

読み込み中…