Acetic Acid → 2-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid methyl ester

HRID 130489

反応式

HRID 130489 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6](N)=[CH:5][CH:4]=1.N([O-])=O.[Na+].[NH2:17][NH2:18].O[C:20]1[C:21](=[O:39])[N:22]([C:32]2[CH:37]=[CH:36][C:35]([I:38])=[CH:34][CH:33]=2)[CH2:23][CH2:24][C:25]=1[C:26](=O)[C:27]([F:30])([F:29])[F:28].[C:40](O)(=O)C>Cl.O>[CH3:40][O:10][C:8](=[O:9])[C:7]1[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[N:17]1[C:20]2[C:21](=[O:39])[N:22]([C:32]3[CH:37]=[CH:36][C:35]([I:38])=[CH:34][CH:33]=3)[CH2:23][CH2:24][C:25]=2[C:26]([C:27]([F:30])([F:29])[F:28])=[N:18]1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 9321HydrazineHCID 2779305-Methoxyanthranilic acidHCID 219368343-hydroxy-1-(4-iodophenyl)-4-(2,2,2-trifluoroacetyl)-5,6-dihydro-1H-pyridin-2-oneHCID 23668193Sodium Nitrite

生成物 1

HCID 693099032-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid methyl ester収率 24%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒2 回HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Part A: To a 0° C. solution of 5-methoxyanthranilic acid (5.0 g, 29.9 mmol) in concentrated hydrochloric acid (10 mL) was added dropwise an ice cold solution of sodium nitrite (2.06 g, 29.9 mmol) in water (5 mL) and stirring was continued at 0° C. for 30 minutes. Stannous chloride dihydrate (16.8 g, 74.8 mmol) was dissolved in concentrated hydrochloric acid (16 mL), cooled to 0° C., and added slowly to the solution of the diazonium salt. The precipitate was agitated, kept at 0° C. for 30 minutes, and then filtered. The solids were washed successively with ice cold brine and petroleum ether and dried under a stream of air and then under vacuum. The crude hydrazine salt and 3-hydroxy-1-(4-iodo-phenyl)-4-(2,2,2-trifluoro-acetyl)-5,6-dihydro-1H-pyridin-2-one (12.3 g, 29.9 mmol) were combined in glacial acetic acid (50 mL) and heated to 80° C. Upon completion of the reaction the solvent was evaporated to a viscous oil which was subjected to silica gel column chromatography to yield 2-[6-(4-iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid methyl ester (4.12 g, 24%). MS (AP+) 571.9 (100%).

後処理

  1. stirringThe precipitate was agitated
  2. waitkept at 0° C. for 30 minutes
  3. filtrationfiltered
  4. washThe solids were washed successively with ice cold brine and petroleum ether
  5. customdried under a stream of air
  6. temperatureheated to 80° C
  7. customUpon completion of the reaction the solvent
  8. customwas evaporated to a viscous oil which

出典と根拠

ORDレコード
ord-11c57d060ab843ceaed0c56790e5a790
出典データセット
uspto-grants-2008_06
特許番号
US07381732B2

関連ノート

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