N-methyl-2-pyrrolidone → 4'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 77779

反応式

HRID 77779 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N:14]3[C:18]([CH3:19])=[N:17][N:16]=[N:15]3)[CH:11]=[C:10]([C:20]([OH:22])=O)[CH:9]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:33][O:34][CH2:35][CH:36]([NH2:38])[CH3:37].CN1C(=O)CCC1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C>[CH3:33][O:34][CH2:35][CH:36]([NH:38][C:20]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:13]=[C:12]([N:14]2[C:18]([CH3:19])=[N:17][N:16]=[N:15]2)[CH:11]=1)=[O:22])[CH3:37]

参加物

8

反応物 5

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 123458MethoxyisopropylamineHCID 578509354'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid

生成物 1

HCID 578512554'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid (0.3402 mmol, 100 mg), HOBt (0.6804 mmol, 91.9 mg), 2-methoxy-1-methyl-ethylamine (0.4083 mmol, 43 μL) and NMP (1.0206 mmol, 112 μL) in CH2Cl2 (1 mL) and DMF (0.5 mL) was added EDCI (0.6804 mmol, 130.4 mg) at room temperature, and the mixture was stirred at room temperature for 18 hours. The mixture was extracted with ethyl acetate and the organic layer was washed with 2N aqueous NaOH, 1 N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by Flash column chromatography, eluting with n-hexane:ethyl acetate (4:1) to give 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (white powder, 90% yield). MS (M+H)=366.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with 2N aqueous NaOH, 1 N aqueous HCl, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Flash column chromatography
  7. washeluting with n-hexane:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-33b87137c5644306b8efb80d7344d64c
出典データセット
uspto-grants-2014_09
特許番号
US08841336B2

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