Water → 4-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide

HRID 498086ノート

反応式

HRID 498086 の反応式
[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:31][C:32]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[N:37]2.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:31][C:32]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]3[C:33]=2[CH:34]=[CH:35][CH:36]=[N:37]3)=[O:19])=[CH:21][CH:22]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acidHCID 122537915-Aminoquinolin-8-ol hydrochloride

生成物 1

HCID 223207184-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide収率 35.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.15 g (0.464 mmol) of compound 2 in CH2Cl2 (2 mL) were added 0.11 g (0.561 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.03 g (0.232 mmol) of 4-dimethylaminopyridine, 2 mL of triethylamine, and 0.16 g (0.695 mmol) of 5-amino-8-hydroxyquinoline HCl salt. After stirring for 24 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1) to give 0.076 g of compound 9 in 35% yield.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1)

出典と根拠

ORDレコード
ord-2f8f8a81da3d4b2c91344163eb668f07
出典データセット
uspto-grants-2005_09
特許番号
US06949654B2

反応ノート

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