Diisopropylethylamine → Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoate

HRID 551983ノート

反応式

HRID 551983 の反応式
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].CCN(C(C)C)C(C)C>C1COCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:39]=[CH:38][C:34]([C:35]([N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]3[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=3)[C:4]([O:6][CH3:7])=[O:5])=[O:36])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 43715358Methyl 2-fluoro-5-(hexylamino)benzoateHCID 575544694-[(4-Butylphenyl)ethynyl]benzoyl chloride

生成物 1

HCID 57554561Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoate収率 128%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (185 mg; 0.73 mmol) in THF (15 mL) were added 4-[(4-butylphenyl)ethynyl]benzoyl chloride (260 mg; 0.88 mmol), DIEA (0.15 mL; 0.88 mmol) and DMAP (20 mg). The mixture was stirred at 60° C. under N2 atmosphere for 1 hour. It was then diluted with DCM (100 mL), washed with HCl 0.1N (50 mL) and a saturated solution of NaHCO3 (100 mL). The organic layer was dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure to give 480 mg of a brown solid. Purification by flash chromatography on silicagel (c-Hex/EtOAc, 90:10) gave 170 mg (45.3%) of the title compound as a white solid. HPLC, Rt: 6.14 min (purity=99.5%). LC/MS: M+(ESI): 514.3.

後処理

  1. washwashed with HCl 0.1N (50 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltrated
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-42a0a95a04cf404086c5ec72d37817c0
出典データセット
uspto-grants-2011_05
特許番号
US07947851B2

反応ノート

読み込み中…