Dimethylformamide → Cyclopropanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide

HRID 449027ノート

反応式

HRID 449027 の反応式
[Cl:1][C:2]1[C:3]([CH:8]([NH2:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH:23]1([C:26](O)=[O:27])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=O)C>>[Cl:1][C:2]1[C:3]([CH:8]([NH:22][C:26]([CH:23]2[CH2:25][CH2:24]2)=[O:27])[C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59341168HCID 59341168、化合物

生成物 1

HCID 86636029Cyclopropanecarboxylic acid [(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-amide収率 120.4%

実験手順

In a 10 mL flask were added C-(3-chloropyrazin-2-yl)-C-(4-phenoxyphenyl)-methylamine (110 mg, 0.00035 mol), cyclopropanecarboxylic acid (0.056 mL, 0.00070 mol), DIEA (0.55 mL, 0.0032 mol), TBTU (0.17 g, 0.00053 mol) and DMF (5 mL, 0.07 mol). The reaction mixture was stirred at rt for 10 min. Reaction was left to stir over weekend. The reaction mixture was concentrated in vacuo, dissolved in DCM and washed with sat aq NaHCO3 followed by brine. The organics were collected and concentrated in vacuo to give 160 mg of the compound as a yellow solid. Purification by prep TLC in 60% EtOAc: hexanes afforded 55 mg of the title compound as a yellow solid. The compound was carried on to the next step. MS (ES+): m/z 380.08 (20)[MH+]. HPLC: tR=3.56 min (Open lynx polar—5 min).

後処理

  1. customReaction
  2. waitwas left
  3. stirringto stir over weekend
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutiondissolved in DCM
  6. washwashed with sat aq NaHCO3
  7. customThe organics were collected
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ed1b348b8f0449a1a19842a04e73d88d
出典データセット
uspto-grants-2013_07
特許番号
US08481733B2

反応ノート

読み込み中…