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 1402587노트

반응식

HRID 1402587 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-8012355d0b9c43d3874614198388f016
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906944B2

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