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

HRID 2264385노트

반응식

HRID 2264385 반응식
[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

참가 물질

8

반응물 4

HCID 8635Methyl AnthranilateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178478382HCID 178478382, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 21226129Dichloromethane methanol용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-47c08bc104eb44ab87618a6b59789872
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855214B2

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