Trifluoroacetic acid → 3-Amino-4-chloro-5-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)benzonitrile

HRID 921943ノート

反応式

HRID 921943 の反応式
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[C:10]([N:16]2[CH2:27][CH2:26][C:19]3([C:23](=[O:24])[N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)[C:9]=1[Cl:28])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[C:12]([CH:11]=[C:10]([N:16]2[CH2:27][CH2:26][C:19]3([C:23](=[O:24])[N:22]([CH3:25])[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)[C:9]=1[Cl:28])[C:14]#[N:15]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 130364299Tert-butyl (2-chloro-5-cyano-3-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl)carbamate

生成物 1

HCID 899231433-Amino-4-chloro-5-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)benzonitrile収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-butyl-(2-chloro-5-cyano-3-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl)carbamate (336 mg, 0.802 mmol) in DCM (3 mL) was treated with TFA (1.174 mL, 15.24 mmol) at room temperature for 2 h. Solvent was evaporated and the residue was redissolved in DCM and concentrated again. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 0-10% methanol/dichloromethane). 3-amino-4-chloro-5-(2-methyl-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)benzonitrile (179 mg) was obtained as alight yellow oil.

後処理

  1. customSolvent was evaporated
  2. dissolutionthe residue was redissolved in DCM
  3. concentrationconcentrated again
  4. additionThe reaction mixture was diluted with dichloromethane
  5. washwashed with saturated sodium bicarbonate
  6. extractionThe aqueous layer was extracted with dichloromethane two more times
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography on silica gel using
  11. washan automated ISCO system (40 g column, eluting with 0-10% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-cdb17ae3868e4fa9874c5c68b6c32494
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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