Acetic Acid → 4-fluoro-3-(7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamido)benzoic acid

HRID 1521332

反応式

HRID 1521332 の反応式
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][C:21](Br)=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[CH:5]=1.[CH3:25][N:26]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[N:27]1.CC(O)=O>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:24])=[CH:5][C:6]=1[NH:11][C:12]([C:14]1[N:18]2[CH:19]=[CH:20][C:21]([C:30]3[N:26]([CH3:25])[N:27]=[CH:28][CH:29]=3)=[CH:22][C:17]2=[N:16][CH:15]=1)=[O:13]

参加物

7

反応物 3

HCID 176Acetic AcidHCID 27600771-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 712828883-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester

生成物 1

HCID 712829094-fluoro-3-(7-(1-methyl-1H-pyrazol-5-yl)imidazo[1,2-a]pyridine-3-carboxamido)benzoic acid

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

3-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic acid methyl ester (step 1) (1200 g, 3.060 mol), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (commercially available) (764 g, 3.67 mol), PdCl2(dppf)•CH2Cl2 (75.0 g, 91.8 mmol) in dioxane (10 L) and aqueous Na2CO3 (2 N, 4.6 L) were heated to reflux for 6 hr. The reaction mixture was cooled to 50° C. and filtered. The filtrate was heated to reflux, to which was added AcOH (600 g, 10.0 mol) was added dropwise. During the course of addition solids came out of solution to give pale pink slurry. After addition the mixture was slowly cooled to RT and filtered. To the filter cake was added dioxane (20 L) followed by heating to reflux to obtain a solution. The solution was cooled to RT and filtered to provide the title compound as a white solid;

後処理

  1. temperatureto reflux for 6 hr
  2. filtrationfiltered
  3. temperatureThe filtrate was heated
  4. temperatureto reflux, to which
  5. additionwas added dropwise
  6. additionDuring the course of addition solids
  7. customto give pale pink slurry
  8. additionAfter addition the mixture
  9. temperaturewas slowly cooled to RT
  10. filtrationfiltered
  11. additionTo the filter cake was added dioxane (20 L)
  12. temperatureby heating
  13. temperatureto reflux
  14. customto obtain a solution
  15. temperatureThe solution was cooled to RT
  16. filtrationfiltered

出典と根拠

ORDレコード
ord-e78e337ad4fc4a4fbda47634f408b91c
出典データセット
uspto-grants-2015_07
特許番号
US09073921B2

関連ノート

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