Ammonia → (5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one

HRID 2207647ノート

反応式

HRID 2207647 の反応式
[NH2:1][C@@:2]1([CH2:9][C:10]#[C:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH2:6][CH2:5][N:4]([CH3:7])[C:3]1=[O:8].N>CC#N.CO.CCOC(C)=O.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:7][N:4]1[CH2:5][CH2:6][C@:2]2([N:1]=[C:11]([C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=4)[CH:15]=[CH:14][N:13]=3)[CH2:10][CH2:9]2)[C:3]1=[O:8]

参加物

7

反応物 2

HCID 222AmmoniaHCID 89648960(3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one

生成物 1

HCID 89648866(5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one収率 74.1%

試薬・触媒・溶媒 4

HCID 76223Silver(I) trifluoromethanesulfonate触媒2 回HCID 887Methanol溶媒2 回HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

Silver trifluoromethanesulphonate (564.86 mg, 2.2 mmol) was added to a solution of (3S)-3-amino-1-methyl-3-[3-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ynyl]pyrrolidin-2-one (which may be prepared as described in Description 107) (4.28 g, 10.99 mmol) in MeCN (60 mL) at 40° C. and the reaction was stirred for 18 hours. Additional AgOTf (10 mol %) was added and stirring was continued for 24 hrs. The solvent was evaporated and the residue was suspended in EtOAc. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated to afford a light brown oil. This was purified using an Isolera, with a (50+100)g SNAP cartridge, eluting with 0 to 100% (mixture of 1% of 2M NH3 in MeOH; 9% MeOH; 90% EtOAc) in EtOAc affording the (5S)-7-methyl-2-[4-[3-(trifluoromethoxy)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (D108) (3.17 g, 8.1414 mmol, 74.1% yield) as a light brown solid;

後処理

  1. stirringstirring
  2. waitwas continued for 24 hrs
  3. customThe solvent was evaporated
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customto afford a light brown oil
  8. customThis was purified

出典と根拠

ORDレコード
ord-b564a0bd099c4374bfd5e43c9ad5f895
出典データセット
uspto-grants-2016_06
特許番号
US09376436B2

反応ノート

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