Trifluoroacetic acid → 2-(4-((S)-3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 2062271ノート

反応式

HRID 2062271 の反応式
C(OC(=O)[NH:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[N:16]=2)[CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:7][CH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH3:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[OH:32])[N:16]=2)[CH2:10]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 136121343tert-Butyl-((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

生成物 1

HCID 1361213552-(4-((S)-3-(Aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To tert-Butyl-((S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate (700 mg, 1.56 mmol) was added 20 mL CH2Cl2 followed by addition of 7 mL of TFA. After the reaction was stirred for 1 hour it was neutralized with a 1.0 M aqueous NaOH solution. The mixture was partitioned between H2O and CH2Cl2, and separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to yield 2-(4-((S)-3-(aminomethyl)piperidin-1-yl)-7-methylquinazolin-2-yl)phenol (400 mg, 74%). LC/MS: m/z 349.3 (M+H)+ at 1.52 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. customThe mixture was partitioned between H2O and CH2Cl2
  2. customseparated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-fa657be2932549b6aa00924892c14f14
出典データセット
uspto-grants-2012_10
特許番号
US08283354B2

反応ノート

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