Triethylamine → 3-[4-(Azetidin-1-ylcarbonyl)-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20605ノート

反応式

HRID 20605 の反応式
[N:1]1([C:5]([C:7]2[CH:33]=[CH:32][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[C:9](Cl)[C:8]=2[F:35])=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>CO>[N:1]1([C:5]([C:7]2[CH:33]=[CH:32][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=3)=[O:16])=[CH:9][C:8]=2[F:35])=[O:6])[CH2:2][CH2:3][CH2:4]1

参加物

4

反応物 2

HCID 8471TriethylamineHCID 115842233-[4-(Azetidin-1-ylcarbonyl)-2-chloro-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

生成物 1

HCID 116557263-[4-(Azetidin-1-ylcarbonyl)-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide収率 39.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-[4-(Azetidin-1-ylcarbonyl)-2-chloro-3-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (162 mg; 0.322 mmol) was dissolved in methanol (10 mL). Triethylamine (97 mg, 0.967 mmol) was added and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (25 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 7 days until completion. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, the filtrate concentrated in vacuo and purified by preparatory reverse phase HPLC using a gradient of 5-95% acetonitrile in water (containing 0.2% TFA) on a Phenomenex Luna 10u C18 (2) 100A column to give the title compound (60 mg).

後処理

  1. customthe flask evacuated
  2. custompurged with nitrogen (3 times)
  3. addition10% Palladium on carbon (25 mg) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with nitrogen (3 times)
  8. filtrationThe catalyst was filtered off
  9. concentrationthe filtrate concentrated in vacuo
  10. custompurified by preparatory reverse phase HPLC

出典と根拠

ORDレコード
ord-abfb473692b4426a8e343784496fa7ca
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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