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Ammonium Chloride → 6-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-cyclopropyl-phenyl)-amide

HRID 1094507
ノート
印刷プレビュー

反応式

HRID 1094507 の反応式
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=2)[NH2:7])[CH2:3][CH2:2]1.C[Al](C)C.C[O:16][C:17]([C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][O:37][CH3:38])[N:31]=3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)=O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:7][C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29][C:30]5[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][O:37][CH3:38])[N:31]=5)=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)=[O:16])[CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 25517Ammonium ChlorideHCID 120321393-CyclopropylanilineHCID 16682925TrimethylaluminumHCID 591759856-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

生成物 1

HCID 236528666-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-cyclopropyl-phenyl)-amide

試薬・触媒・溶媒 4

HCID 962
Water
溶媒
HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
10 °C

実験手順

In a dried vessel, 32.8 mg (0.247 mMol) 3-cyclopropyl-aniline [preparation see: Tet. Lett. 43 (2002) 6987] are dissolved in 4.3 ml toluene and cooled to 10° C. Then 370 μl Me3Al (2 M in toluene; 0.74 mMol) are added via syringe. After 1 h at rt, a solution of 80 mg (0.247 mMol) 6-(2-methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester (Step 15.4) in 1 ml THF is added and the reaction mixture is stirred for 30 min in an oil bath of 110° C. The solution is cooled in ice and hydrolyzed with 11 ml of a sat. NH4Cl. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; toluene/acetone 99:1→4:1) gives the title compound: MS: [M+1]+=426; TLC (toluene/acetone 4:1): Rf=0.09.

後処理

  1. stirringAfter 15 min stirring
  2. customthe aq. phase separated off
  3. extractionextracted with EtOAc
  4. washThe organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ef89e87ade3f4b2b8f84421b0ac5f646
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08133886B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート