1,2-Dichloroethane → N-(4-Methyl-3-pyridinyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623793ノート

反応式

HRID 1623793 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][C:40]=1[NH2:45]>CN(C)C=O.O.CC#N>[CH3:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][C:40]=1[NH:45][C:11](=[O:12])[C:10]1[CH:14]=[C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:9]=1[O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1379353-Amino-4-picolineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

生成物 1

HCID 69937017N-(4-Methyl-3-pyridinyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 110 mg, 0.33 mmol), EDC (126 mg, 0.66 mmol) and HOBT (101 mg, 0.66 mmol) in dimethylformamide (2 ml) stirred in air at room temperature for 1 h. 4-Methylpyridin-3-amine (35.6 mg, 0.33 mmol) was then added in one charge. The reaction mixture was stirred at 25° C. overnight. The reaction mixture was diluted with water (25 ml), and then extracted with ethyl acetate (60 ml×3). The organic phases were combined, washed with brine (50 ml×3), dried over anhydrous MgSO4 and concentrated. The residue was purified by Prep-HPLC (instrument: Gilson GX-281, Column: Shimadzu 15 μm, 250×20 mm×2, Mobile Phase: A=10 mmol NH4HCO3/water B=CH3CN, Flow rate: 30.0 ml/L method: B=55%-65%, 0.0-7.2 min; B=65%-95%, 7.2-7.5 min; B=95%-95%, 7.5 min-11.5 min, the RT=10.0 min) to yield the title compound as a pink solid. 94 mg.

後処理

  1. additioncharge
  2. extractionextracted with ethyl acetate (60 ml×3)
  3. washwashed with brine (50 ml×3)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by Prep-HPLC (instrument
  7. customB=55%-65%, 0.0-7.2 min
  8. customB=65%-95%, 7.2-7.5 min

出典と根拠

ORDレコード
ord-644421b0b0684390a2a613d070fadde2
出典データセット
uspto-grants-2014_07
特許番号
US08778939B2

反応ノート

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