Hydrochloric Acid → 3-[1-(6-Ethoxy-7-hydroxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline

HRID 617157ノート

反応式

HRID 617157 の反応式
[H-].[Na+].C1(S)C=CC=CC=1.Cl.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24]CC)[N:20]=[C:19]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:18]=[C:17]2[N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:48](=[O:49])[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([CH3:50])[CH:46]=3)[N:41]([CH3:51])[C:40]2=[O:52])[CH2:35][CH2:34]1)[CH3:12].Cl>CN(C=O)C.O>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[OH:24])[N:20]=[C:19]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:18]=[C:17]2[N:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:48](=[O:49])[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([CH3:50])[CH:46]=3)[N:41]([CH3:51])[C:40]2=[O:52])[CH2:35][CH2:34]1)[CH3:12]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 99388233-[1-(6,7-Diethoxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline hydrochloride

生成物 1

HCID 1358228343-[1-(6-Ethoxy-7-hydroxy-2-morpholino-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-1,6-dimethyl-2,4-dioxoquinazoline収率 49%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

In 10 ml of DMF was suspended 1.19 g (30.0 mmol) of 60% sodium hydride, and 3.07 ml (30.0 mmol) of thiophenol in 20 ml of DMF was dropwised under ice-cooling. After the mixture was stirred at ice-cooling for 10 minutes, 5.74 g (10.0 mmol) of Compound 10 obtained in Example 10 in DMF (50 ml) was added at ice-cooling, then the reaction mixture was stirred at 150° C. for 20 hours. After the reaction mixture was cooled to room temperature, water was added, pH of the reaction mixture was adjusted at 5 by concentrated hydrochloric acid and was subjected to extraction with chloroform. The organic layer was washed with sodium chloride solution and dried, concentrated to give residue which was purified by silica gel column chromatography (eluent: chloroform/methanol=50/1). The more polar product obtained was recrystallized from ethanol/ether to give 2.67 g (yield: 49%) of Compound 47 as white crystals.

後処理

  1. temperaturecooling
  2. temperaturecooling for 10 minutes
  3. temperaturecooling
  4. stirringthe reaction mixture was stirred at 150° C. for 20 hours
  5. extractionwas subjected to extraction with chloroform
  6. washThe organic layer was washed with sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customto give residue which
  10. customwas purified by silica gel column chromatography (eluent: chloroform/methanol=50/1)
  11. customThe more polar product obtained
  12. customwas recrystallized from ethanol/ether

出典と根拠

ORDレコード
ord-5199e45a13c646aeb680c0b3843f27de
出典データセット
uspto-grants-1999_09
特許番号
US05948784

反応ノート

読み込み中…