Potassium Carbonate → HCID 67479155, 화합물

HRID 472545노트

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HRID 472545 반응식
[NH2:1][C:2]1[N:11]=[C:5]2[C:6]([OH:10])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.ClCCl>[Cl:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][O:10][C:6]1[C:5]2[N:4]([N:3]=[C:2]([NH2:1])[N:11]=2)[CH:9]=[CH:8][CH:7]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 67481450HCID 67481450, 화합물

생성물 1

HCID 67479155HCID 67479155, 화합물

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

260 c) 2-Amino-[1,2,4]triazolo[1,5-a]pyridin-8-ol (0.200 g, 1.33 mmol) was suspended in acetone (1.9 mL). 1-(bromomethyl)-3-chloro-benzene (0.184 mL, 1.40 mmol) and potassium carbonate (193 mg, 1.40 mmol) were added and the reaction mixture was heated to 80° C. for 1 hour. Reaction mixture was cooled to room temperature, diluted with water, extracted with dichloromethane, dried over magnesium sulfate, filtered, and concentrated. Resulting oil was taken up in dichloromethane and purified via chromatography (silica gel 0-100% ethyl acetate in hexanes). 8-(3-Chloro-benzyloxy)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was isolated as an oil which solidified on standing. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.17 (d, J=6.6 Hz, 1H), 7.56 (s, 1H), 7.44-7.42 (m, 3H), 6.99 (d, J=7.9 Hz, 1H), 6.79-6.75 (m, 1H), 5.94 (bs, 2H), 5.30 (s, 2H). MS=275 (MH)+. 260 d) [8-(3-Chloro-benzyloxy)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 8-(3-chloro-benzyloxy)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (95.0 mg, 0.346 mmol) and 1-(4-bromo-phenyl)-4-methyl-piperazine (102 mg, 0.399 mmol in a manner analogous to Example 2d. Product was isolated as a pale orange solid (0.073 g, 47%). MP=135-138° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.33 (s, 1H), 8.37 (d, J=6.7 Hz, 1H), 7.58 (s, 1H), 7.51-7.44 (m, 5H), 7.09 (d, J=7.9 Hz, 1H), 6.91-6.86 (m, 3H), 5.35 (s, 2H), 3.04-3.01 (m, 4H), 2.46-2.44 (m, 4H), 2.22 (s, 3H). MS=449 (MH)+.

후처리

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResulting oil
  8. custompurified via chromatography (silica gel 0-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-56d47468372145318cd9a8fa397c3295
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

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