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Dimethylformamide → 4-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl ester

HRID 1199297
ノート
印刷プレビュー

反応式

HRID 1199297 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[CH:19]=[CH:20][CH2:21][OH:22])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)=[O:28].C1(N=C=NC2CCCCC2)CCCCC1.CN(C=O)C>CN(C)C1C=CN=CC=1.O.CCOCC>[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:22][CH2:21][CH:20]=[CH:19][CH:18]([O:17][C:16]2[CH:15]=[CH:14][C:13]([O:12][C:7]3[CH:6]=[N:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=3)=[CH:25][CH:24]=2)[CH3:23])=[O:34])=[CH:31][CH:30]=1)=[O:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide2 回HCID 5060574-Carbamoylbenzoic acid2 回HCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

生成物 1

HCID 569955344-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl ester収率 26%

試薬・触媒・溶媒

3
HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 1.5 g (4.2 mmol) of the pentenol obtained in Example 3 above, 1.04 g (6.3 mmol) of 4-(aminocarbonyl)benzoic acid, 1.30 g (6.3 mmol) of dicyclohexylcarbodiimide (DCC), 0.05 g of 4-(dimethylamino)pyridine and 20 ml of DMF was stirred at room temperature overnight. An additional 0.3 g of DCC and 0.25 g of 4-(aminocarbonyl)benzoic acid are added and the mixture was stirred an additional 20 hours. The mixture was then poured into ether, water added and filtered. The filtrates were separated, and the organic layer washed with saturated aqueous NaHC03 and water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with a 3:2 hexane:acetone, mixture to give 0.55 g of the desired product as a tan, glassy solid, m.p. 144°-148° C. (Compound 22).

後処理

  1. stirringthe mixture was stirred an additional 20 hours
  2. additionadded
  3. filtrationfiltered
  4. customThe filtrates were separated
  5. washthe organic layer washed with saturated aqueous NaHC03 and water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was purified by preparative scale HPLC
  9. washeluting with a 3:2 hexane

出典と根拠

ORDレコード
ord-3ef4e604f1434ab8b250b2621fbb685e
出典データセット
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04900354

反応ノート

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