Diisopropylethylamine → Ethyl 4'-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)biphenyl-3-carboxylate

HRID 1845170

反応式

HRID 1845170 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:19](O)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:45][C:46]1[N:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][N:47]=1.C(N(CC)C(C)C)(C)C>C([O-])(O)=O.[Na+].CCOC(C)=O.C(Cl)Cl>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:8]([C:19](=[O:20])[NH:53][CH2:52][C:49]3[CH:48]=[N:47][C:46]([CH3:45])=[N:51][CH:50]=3)[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=2)=[CH:13][CH:14]=1

参加物

9

反応物 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21294601(2-Methylpyrimidin-5-yl)methanamineHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

生成物 1

HCID 44223019Ethyl 4'-methyl-5-((2-methylpyrimidin-5-yl)methylcarbamoyl)biphenyl-3-carboxylate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of crude 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (450 mg, 1.6 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (610 mg, 3.2 mmol), 1-hydroxybenzotriazole hydrate (240 mg, 1.6 mmol), CH2Cl2 (5 mL) were added (2-methylpyrimidin-5-yl)methanamine (290 mg, 2.4 mmol) and N,N-diisopropylethylamine (0.41 mL, 2.4 mmol). The reaction mixture was stirred at room temperature overnight, and then diluted with aq. NaHCO3 solution and EtOAc (100 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column (0-20% MeOH/CH2Cl2) to afford the title product as a white foam.

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column (0-20% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-97d7561a4eaa4f94bb3082982c572994
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

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