Diisopropylethylamine → 1-{2-(Hex-5-enylmethylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarbonyl}amino-2-vinylcyclopropanecarboxylic acid ethyl ester

HRID 579641노트

반응식

HRID 579641 반응식
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=C(C4C=CC=C(C)N=4)[CH:21]=3)[CH2:16][CH:15]2[C:40](O)=[O:41])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].Cl.[CH3:44][NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51].[CH:52]([N:55]([CH:58]([CH3:60])[CH3:59])CC)([CH3:54])[CH3:53].[CH3:61]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:60]([C:58]4[CH:59]=[CH:61][CH:54]=[C:52]([CH3:53])[N:55]=4)[CH:21]=3)[CH2:16][CH:15]2[C:40](=[O:41])[N:45]([CH2:46][CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51])[CH3:44])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668720342-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acidHCID 71413963N-Methylhex-5-en-1-amine hydrochloride

생성물 1

HCID 668720481-{2-(Hex-5-enylmethylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarbonyl}amino-2-vinylcyclopropanecarboxylic acid ethyl ester수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-(1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acid (99, 0.77 g, 1.344 mmol), N-methylhex-5-enylamine hydrochloride (221 mg, 1.95 mmol) and diisopropylethylamine (1.17 mL, 6.72 mmol) in DMF (25 mL) was stirred at 0° C. under inert atmosphere. After 30 min HATU (741 mg, 1.95 mmol) was added and the reaction mixture was allowed to warm up to room temperature overnight. Then, DMF was evaporated and the residue was partitioned between AcOEt and a solution of NaHCO3. Organic layer was successively washed with water and brine, dried (MgSO4), filtered and evaporated. The crude product was purified by silica gel chromatography (gradient Heptane/AcOEt 80:20 to 50:50) to give 735 mg (82%) of the title compound: m/z=669 (M+H)+.

후처리

  1. customThen, DMF was evaporated
  2. customthe residue was partitioned between AcOEt
  3. washOrganic layer was successively washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography (gradient Heptane/AcOEt 80:20 to 50:50)

출처 및 근거

ORD 기록
ord-b373ff611f164c4d9e3fb35d33eb7082
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040562B2

반응 노트

불러오는 중…