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1-Hydroxybenzotriazole → N-({2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methyl)tetrahydro-2H-pyran-4-carboxamide

HRID 38786
ノート
印刷プレビュー

反応式

HRID 38786 の反応式
[NH2:1][CH2:2][C:3]1[C:4]([C:17]([F:20])([F:19])[F:18])=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[N:7][CH:8]=1.[O:21]1[CH2:26][CH2:25][CH:24]([C:27](O)=[O:28])[CH2:23][CH2:22]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.ClCCl>[Cl:16][C:12]1[CH:11]=[C:10]([NH:9][C:6]2[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]([CH2:2][NH:1][C:27]([CH:24]3[CH2:25][CH2:26][O:21][CH2:22][CH2:23]3)=[O:28])=[CH:8][N:7]=2)[CH:15]=[CH:14][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 219302Oxane-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 115875365-(aminomethyl)-N-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine

生成物 1

HCID 58168800N-({2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methyl)tetrahydro-2H-pyran-4-carboxamide
収率 29%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 5-(aminomethyl)-N-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine (103 mg) and dichloromethane (2 mL) were added tetrahydro-2H-pyran-4-carboxylic acid (53 mg), 1-hydroxybenzotriazole (69 mg), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (98 mg) in this order at room temperature, and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added ethyl acetate (50 mL), the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol), and the obtained product was solidified from a mixed solvent of ethanol and ethyl acetate to obtain N-({2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}methyl)tetrahydro-2H-pyran-4-carboxamide (41 mg) as a colorless powder.

後処理

  1. washthe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

出典と根拠

ORDレコード
ord-a1de4ce8f0f245628732eb92c2f594c4
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524727B2

反応ノート

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