Diethylene Glycol → 6-((6-Phenylimidazo[1,2-b]pyridazin-3-yl)methyl)quinoline

HRID 40331

反応式

HRID 40331 の反応式
O.NN.[C:4]1([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=O)=[CH:17][N:18]=3)[N:15]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[K+].C(O)COCCO>O>[C:4]1([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([CH2:19][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[CH:17][N:18]=3)[N:15]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 67502844(6-Phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

生成物 1

HCID 442069676-((6-Phenylimidazo[1,2-b]pyridazin-3-yl)methyl)quinoline

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 10-20 mL microwave vial was charged with hydrazine hydrate (0.0312 ml, 0.642 mmol), (6-phenylimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone (0.150 g, 0.428 mmol), KOH (0.0961 g, 1.71 mmol), and diethylene glycol (4.09 ml, 42.8 mmol), sealed, then placed in a Personal Chemistry microwave at 130° C. for 20 minutes after a 5 minute pre-stir. The mixture was diluted with water (75 mL), then extracted with DCM (2×75 mL). The combined organics were washed with brine (75 mL), then dried with MgSO4, filtered, and concentrated to give a brown solid, then purified by prep HPLC to give the product as the formic acid salt. MS (ESI pos. ion) m/z: 337 (MH+). Calc'd exact mass for C22H16N4: 336.

後処理

  1. customsealed
  2. extractionextracted with DCM (2×75 mL)
  3. washThe combined organics were washed with brine (75 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown solid
  8. custompurified by prep HPLC
  9. customto give the product as the formic acid salt

出典と根拠

ORDレコード
ord-28352e1f17c84e3ea4d08500c9d5cdf7
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

関連ノート

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