Trifluoroacetic acid → (S)-1-(4-Methyl-2'-(trifluoromethyl)-[3,4'-bipyridin]-6-yl)ethan-1-amine

HRID 57502

反応式

HRID 57502 の反応式
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[C:12]([CH3:26])[CH:11]=1)[CH3:9])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:26][C:12]1[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[N:15]=[CH:14][C:13]=1[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 90451687tert-butyl (S)-(1-(4-methyl-2'-(trifluoromethyl)-[3,4'-bipyridin]-6-yl)ethyl)carbamate

生成物 1

HCID 90423562(S)-1-(4-Methyl-2'-(trifluoromethyl)-[3,4'-bipyridin]-6-yl)ethan-1-amine収率 99.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-tert-butyl(1-(4-methyl-2′-(trifluoromethyl)-[3,4′-bipyridin]-6-yl)ethyl)carbamate (200 mg, 0.524 mmol) in DCM (2 ml) at −78° C. was added trifluoroacetic acid (2 mL, 12.98 mmol). The solution was stirred at r.t. for 1 hr. The mixture was concentrated, diluted with 10 mL DCM and stirred with solid MP-carbonate to remove TFA. Filtered and concentrated to give 147 mg (S)-1-(4-methyl-2′-(trifluoromethyl)-[3,4′-bipyridin]-6-yl)ethanamine as a light brown sticky oil. MS m/z 282.1 (M+H). Rt=0.85 min. (Column: XBridge C18 3.5 um 2.1×50 mm. Solvent A: 2% Acetonitrile, 3.75 mM Ammonium Acetate, Water. Solvent B: Acetonitrile. Gradient: 5-95% B over 1.70 min. Flow rate: 2 mL/min.) The crude product was used to next step without further purification.

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 10 mL DCM
  3. stirringstirred with solid MP-carbonate
  4. customto remove TFA
  5. filtrationFiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f79611c2ca09411da2304cdfa819ecd5
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

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