Trifluoroacetic acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine

HRID 242900ノート

反応式

HRID 242900 の反応式
C(OC(=O)[NH:7][C@H:8]([C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:8]([NH2:7])[CH2:9][CH3:10])[N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=2[CH:22]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68158046(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate

生成物 1

HCID 68157917(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine収率 25%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (234 mg, 0.63 mmol) in DCM (3 mL) was added TFA (1.5 mL) and the mixture stirred at RT for 2 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM (20 mL) and a saturated aqueous solution of NaHCO3. The two phase system was stirred for 10 min, then the organic fraction dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a colourless oil (42 mg, 25%). LCMS (Method B): RT 1.90 min [M−NH2]+ 253.0.

後処理

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM (20 mL)
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic fraction dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-8413817172844815806aaead5001f251
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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