1-Hydroxybenzotriazole → 4-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-pyridine

HRID 1172918ノート

反応式

HRID 1172918 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([NH:7][OH:8])=[NH:6].[CH3:16][C:17]1[CH:25]=[N:24][CH:23]=[CH:22][C:18]=1[C:19](O)=O.C1C=CC2N(O)N=NC=2C=1.N=C=N.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]=[C:19]([C:18]3[CH:22]=[CH:23][N:24]=[CH:25][C:17]=3[CH3:16])[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14]

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 15020033-Methyl-isonicotinic acidHCID 178458441HCID 178458441、化合物

生成物 1

HCID 595566694-[3-(3-Chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-pyridine収率 10.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
160 °C

実験手順

To a microwave vial charged with 3-chloro-N-hydroxy-4-isopropoxy-benzamidine (75 mg, 0.328 mmol), 3-methyl-isonicotinic acid (41 mg, 0.298 mmol), HOBt (46 mg, 0.298 mmol), PS-carbodiimide (720 mg, 0.894 mmol, loading 1.24 mmol/g) was added acetonitrile (3.5 mL) and diisopropylethylamine (156 μL, 0.894 mmol). The reaction vial was capped and heated at about 160° C. for about 30 minutes in a Biotage microwave. The reaction mixture was filtered and the resin was washed with acetonitrile (4 mL). Filtrate was concentrated to dryness. The crude product was purified via reverse phase HPLC (30-90% acetonitrile, 30 minute ramp) to give 10.2 mg (10%) of 4-[3-(3-chloro-4-isopropoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-pyridine.

後処理

  1. customThe reaction vial was capped
  2. filtrationThe reaction mixture was filtered
  3. washthe resin was washed with acetonitrile (4 mL)
  4. concentrationFiltrate was concentrated to dryness
  5. customThe crude product was purified via reverse phase HPLC (30-90% acetonitrile, 30 minute ramp)

出典と根拠

ORDレコード
ord-4dc39e01fa6242ba936217e2a406435d
出典データセット
uspto-grants-2010_11
特許番号
US07834039B2

反応ノート

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