Pyridine → 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

HRID 2278630ノート

反応式

HRID 2278630 の反応式
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.[N:33]1([C:39]2[N:40]=[C:41]([CH2:46][C:47]([O-])=[O:48])[NH:42][C:43](=[O:45])[CH:44]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.[Na+]>CN(C)C=O>[N:33]1([C:39]2[N:40]=[C:41]([CH2:46][C:47](=[O:48])[N:14]3[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:10]4([CH2:11][CH2:12][O:7][CH2:8][CH2:9]4)[CH2:13]3)[NH:42][C:43](=[O:45])[CH:44]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1

参加物

6

反応物 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 589750752',3',5',6'-Tetrahydrospiro[indoline-3,4'-pyran]HCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

生成物 1

HCID 1360696186-(morpholin-4-yl)-2-[2-oxo-2-(2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)ethyl]pyrimidin-4(3H)-one収率 78.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 679 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, 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 25 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. 640 mg of 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:

後処理

  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

出典と根拠

ORDレコード
ord-a3e40332f7604859b0f72e65e47512e7
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

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