Triethylamine → 3-{[4-(Azetidin-1-ylcarbonyl)phenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

HRID 20528ノート

反応式

HRID 20528 の反応式
[N:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:34])[CH2:32][OH:33])[CH:29]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH2:25][CH3:26])[N:21]=3)=[O:18])=[C:9](Cl)[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>C1COCC1.CO>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:27]=[C:28]([O:30][C@@H:31]([CH3:34])[CH2:32][OH:33])[CH:29]=3)[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22]([CH2:25][CH3:26])[N:21]=3)=[O:18])=[CH:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 8471TriethylamineHCID 117130403-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide

生成物 1

HCID 116268333-{[4-(Azetidin-1-ylcarbonyl)phenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide収率 73%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-{[4-(azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-N-(1-ethyl-1H-pyrazol-3-yl)-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzamide (246 mg, 0.504 mmol) and triethylamine (0.42 mL, 3.02 mmol) in THF (6 mL) and methanol (6 mL) was evacuated and purged with argon (×3). Palladium on carbon (10% w/w, 52 mg) was added and reaction mixture was evacuated and finally filled with hydrogen gas. The reaction mixture was left to stir at ambient temperature under hydrogen for 2 hours. The Pd/C was filtered off and mixture partitioned between ethyl acetate and 1M hydrochloric acid solution. The organic phase was dried (MgSO4) and the filtrate concentrated in vacuo to give the product (170 mg, 73%).

後処理

  1. custompurged with argon (×3)
  2. additionPalladium on carbon (10% w/w, 52 mg) was added
  3. customreaction mixture
  4. customwas evacuated
  5. additionfinally filled with hydrogen gas
  6. waitThe reaction mixture was left
  7. filtrationThe Pd/C was filtered off
  8. custommixture partitioned between ethyl acetate and 1M hydrochloric acid solution
  9. dry with materialThe organic phase was dried (MgSO4)
  10. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-3ea83e182c104d1a8c4d70ce0973c303
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

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