Methyl Anthranilate → 5-(5-cyclopropyl-2H-pyrazol-3-ylamino)-1,2,3,4-tetrahydro-quinazolino[3,2-a]quinazolin-12-one hydrochloride

HRID 2264385ノート

反応式

HRID 2264385 の反応式
[Cl:1][CH:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[NH:3]1.[C:21](OC)(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH2:24].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.ClCCl.Cl.CO>[ClH:1].[CH:18]1([C:16]2[CH:17]=[C:13]([NH:12][C:10]3[C:9]4[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=4[N:3]4[C:21](=[O:29])[C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=[C:2]4[N:11]=3)[NH:14][N:15]=2)[CH2:20][CH2:19]1

参加物

8

反応物 4

HCID 8635Methyl AnthranilateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178478382HCID 178478382、化合物

生成物 1

HCID 1784796005-(5-cyclopropyl-2H-pyrazol-3-ylamino)-1,2,3,4-tetrahydro-quinazolino[3,2-a]quinazolin-12-one hydrochloride収率 7.1%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

(2-Chloro-1,2,5,6,7,8-hexahydro-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (150 mg, 0.518 mmol), in methyl anthranilate (0.1 ml, 0.777 mmol) was heated to 135° C. for 4 hours to give a brown gum. This was dissolved in methanol/dichloromethane and added to a mixture of ethyl acetate and aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the extracts dried over magnesium sulphate and concentrated. Purification by flash chromatography on silica gel eluting with 4% methanol/dichloromethane gave a pale yellow gum. This was dissolved in 0.5M HCl in methanol and crystallised by the dropwise addition of diethyl ether to give cream coloured crystals of 5-(5-cyclopropyl-2H-pyrazol-3-ylamino)-1,2,3,4-tetrahydro-quinazolino[3,2-a]quinazolin-12-one hydrochloride (15 mg, 7%).

後処理

  1. customto give a brown gum
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts dried over magnesium sulphate
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel eluting with 4% methanol/dichloromethane
  6. customgave a pale yellow gum
  7. customcrystallised by the dropwise addition of diethyl ether

出典と根拠

ORDレコード
ord-47c08bc104eb44ab87618a6b59789872
出典データセット
uspto-grants-2010_12
特許番号
US07855214B2

反応ノート

読み込み中…