Trifluoroacetic acid → 4-[[4-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]aniline

HRID 1675033ノート

反応式

HRID 1675033 の反応式
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:41])([F:40])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([NH:32]C(=O)OC(C)(C)C)=[CH:28][CH:27]=4)[CH2:21][CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>C(Cl)Cl>[F:41][C:9]([F:8])([F:40])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:20][CH2:21][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=4)[CH2:23][CH2:24]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67339893HCID 67339893、化合物

生成物 1

HCID 591497504-[[4-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]aniline収率 56.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TFA (0.5 mL, 0.15 mmol) was added to tert-butyl N-[4-[[4-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]phenyl]carbamate (obtained as described in Example 146, 72 mg, 0.15 mmol) in DCM (2 mL). The resulting solution was stirred at ambient temperature for 2 hours and then evaporated to dryness. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 0.1% TFA) and MeCN as eluents. Fractions containing the desired compound were evaporated and further purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness to afford 4-[[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]aniline (32 mg, 56%).

後処理

  1. customevaporated to dryness
  2. customThe crude product was purified by preparative HPLC
  3. additionFractions containing the desired compound
  4. customwere evaporated
  5. customfurther purified by ion exchange chromatography
  6. washThe desired product was eluted from the column
  7. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-515b3e422faf4792a5e48bd7f9ec9885
出典データセット
uspto-grants-2011_08
特許番号
US08003649B2

反応ノート

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