Pyridine → US9133168, Example 22d

HRID 2278631노트

반응식

HRID 2278631 반응식
N1C=CC=CC=1.[O:7]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH2:13]2)[CH2:9][CH2:8]1.Cl.CN(C)CCCN=C=NCC.[CH3:33][N:34]1[C:39](=[O:40])[CH:38]=[C:37]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[N:36]=[C:35]1[CH2:47][C:48]([O-])=[O:49].[Na+]>CN(C)C=O>[CH3:33][N:34]1[C:39](=[O:40])[CH:38]=[C:37]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[N:36]=[C:35]1[CH2:47][C:48](=[O:49])[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]2([CH2:11][CH2:12][O:7][CH2:8][CH2:9]2)[CH2:13]1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetateHCID 589750752',3',5',6'-Tetrahydrospiro[indoline-3,4'-pyran]

생성물 1

HCID 57389784US9133168, Example 22d수율 5.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3.8 ml of pyridine, 378 mg of 1,2,2′,3′,5′,6′-hexahydrospiro[3H-indole-3,4′-[4H]pyran] and 575 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 770 mg of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 4d, step 2d) in 11.3 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 16 hours, and then concentrated under reduced pressure. The residue is taken up in 15 ml of water and 20 ml of ethyl acetate, and then left to stir at ambient temperature for 1 hour. The precipitate formed is filtered off, and then rinsed successively with water and diethyl ether. 45 mg of 3-methyl-6-(morpholin-4-yl)-2-[2-oxo-2-(2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-pyran]-1(2H)-yl)ethyl]pyrimidin-4(3H)-one are thus obtained in the form of an off-white powder, the characteristics of which are the following:

후처리

  1. concentrationconcentrated under reduced pressure
  2. wait20 ml of ethyl acetate, and then left
  3. stirringto stir at ambient temperature for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed successively with water and diethyl ether

출처 및 근거

ORD 기록
ord-273d9b1aedb34fecb67f514095f2f8e9
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133168B2

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