Ethylamine → N,N'-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide

HRID 1402587ノート

反応式

HRID 1402587 の反応式
[F:1][C:2]1[CH:31]=[CH:30][C:29]([C:32]([NH:34][C:35]2[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=2[F:42])=[O:33])=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:15][CH:14]=[C:13]([C:16]([NH:18][CH:19]([CH2:23][CH2:24][C:25]([OH:27])=O)[C:20](O)=[O:21])=[O:17])[CH:12]=2)[CH:6]=1.Cl.C[N:45](C)[CH2:46][CH2:47]CN=C=NCC.[CH2:55]([NH2:57])[CH3:56].C1COCC1>CN(C=O)C.O>[CH2:55]([NH:57][C:20](=[O:21])[CH:19]([NH:18][C:16]([C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]([O:4][C:3]3[CH:28]=[C:29]([C:32]([NH:34][C:35]4[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=4[F:42])=[O:33])[CH:30]=[CH:31][C:2]=3[F:1])[CH:10]=[CH:9][N:8]=2)[NH:15][CH:14]=1)=[O:17])[CH2:23][CH2:24][C:25]([NH:45][CH2:46][CH3:47])=[O:27])[CH3:56]

参加物

7

反応物 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712935772-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid

生成物 1

HCID 71293595N,N'-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid (100 mg, 0.17 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, 83 mg, 0.43 mmol) in 10 ml of anhydrous DMF was added 2M ethylamine solution in THF (0.43 ml, 0.86 mmol). The mixture was stirred at room temperature for overnight and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 5-8% of methanol in chloroform to afford N,N′-diethyl-2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanediamide as white solid. Yield: 76 mg, 69%.

後処理

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo
  4. customto give the crude, which
  5. customwas purified by silica gel chromatography
  6. washeluting with 5-8% of methanol in chloroform

出典と根拠

ORDレコード
ord-8012355d0b9c43d3874614198388f016
出典データセット
uspto-grants-2014_12
特許番号
US08906944B2

反応ノート

読み込み中…