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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one

HRID 2278627
ノート
印刷プレビュー

反応式

HRID 2278627 の反応式
[N:1]1([C:7]2[N:12]=[C:11]([CH2:13][C:14](=[O:33])[N:15]3[C:23]4[C:18](=[C:19](C5CCCN(CCC)C5)[CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[NH:10][C:9](=[O:34])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.CN(C)[CH2:38][CH2:39][CH2:40]N=C=NCC.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+]>CN(C)C=O.N1C=CC=CC=1>[N:1]1([C:7]2[N:12]=[C:11]([CH2:13][C:14](=[O:33])[N:15]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH:17]4[CH2:38][CH2:39][CH2:40][CH:16]34)[NH:10][C:9](=[O:34])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 1360696076-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

生成物 1

HCID 1360696136-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one収率 143.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒

実験手順

320 mg of 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole [reference example 7d] and 424 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are added to a solution of 525 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (obtained in step 2d of example 1d) in 4 ml of N,N-dimethylformamide and 4 ml of pyridine. The reaction mixture is stirred at ambient temperature for 72 hours and then concentrated under reduced pressure. The residue is taken up in a mixture of water and ethyl acetate and the organic phase is washed successively with water, a 1M hydrochloric acid solution and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is triturated from methanol, filtered and washed with diisopropyl ether, so as to give 375 mg of 6-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one, the characteristics of which are the following:

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is taken up in a mixture of water and ethyl acetate
  3. washthe organic phase is washed successively with water
  4. dry with materiala 1M hydrochloric acid solution and water, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is triturated from methanol
  8. filtrationfiltered
  9. washwashed with diisopropyl ether

出典と根拠

ORDレコード
ord-2f20f541b9e640b986b009bc55ace125
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133168B2

反応ノート

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