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Hydrochloric Acid → 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HCl

HRID 613277
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HRID 613277 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[ClH:16]
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 14923Ammonium HydroxideHCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 700874611-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.HCl수율 59.3%

시약·촉매·용매 3

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매
HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

A mixture of 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b] quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and benzylamine (0.98 ml, 9 mmol) was heated at 80° C. overnight. The reaction mixture was poured into water (100 ml), then NH4OH (0.5 ml) was added. The mixture was extracted with CH2Cl2 (200 ml) and the CH2Cl2 was concentrated to about 20 ml and then this solution was purified by column chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% ethyl acetate/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl. The mixture was evaporated and the residue was crystallized from ether to afford 0.9 g of 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine·HCl, as an off white solid, m.p. 228-231° C.

후처리

  1. extractionThe mixture was extracted with CH2Cl2 (200 ml)
  2. concentrationthe CH2Cl2 was concentrated to about 20 ml
  3. customthis solution was purified by column chromatography on silica gel
  4. washeluting with 20% ethyl acetate/hexane
  5. customto afford the product as the free base
  6. customThe mixture was evaporated
  7. customthe residue was crystallized from ether

출처 및 근거

ORD 기록
ord-9a7d3f81d303490bad8a0f632ae59596
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06008226

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