Hydrazine → 2-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethanol

HRID 1711793ノート

反応式

HRID 1711793 の反応式
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[N:19][C:20]([NH:23][NH2:24])=[CH:21][CH:22]=1)[CH:14]=[CH:13][O:12]2.FC1C=CC(C2N=C3N(C=2)C=CO3)=CC=1.[CH2:40]1C(=O)N(I)[C:42](=[O:43])[CH2:41]1.FC1C=CC(B(O)O)=CN=1.NN.[Si](OCCC=O)(C(C)(C)C)(C)C.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][C:20]4[N:19]([C:40]([CH2:41][CH2:42][OH:43])=[N:24][N:23]=4)[CH:18]=2)[CH:14]=[CH:13][O:12]3)=[CH:2][CH:7]=1

参加物

9

反応物 7

HCID 9321HydrazineHCID 120273N-IodosuccinimideHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalHCID 12217721Iodo benzene diacetateHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazoleHCID 594578146-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole

生成物 1

HCID 594578032-(6-(6-(4-Fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethanol収率 14%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

The 6-(2,4-difluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole (0.20 g, 0.65 mmol; prepared using A from 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3] with NIS, C with 2-fluoropyridine-5-boronic acid [Asymchem], D with hydrazine) and 3-(tert-butyldimethylsilyloxy)propanal (0.12 g, 0.65 mmol; Toronto) were dissolved in MeOH (5.0 mL) and heated to about 65° C. for about 1 h. The MeOH was evaporated then DCM (5 mL) was added followed by iodobenzene diacetate (0.21 g, 0.65 mmol). The reaction was stirred for about 16 h and then evaporated. The resulting solid was dissolved in 1M TBAF in THF (5 mL). The reaction was allowed to stir for about 30 min. The THF was evaporated and the crude material was purified by reverse phase HPLC (Table 1, Method f). The fractions containing product were concentrated under reduced pressure and the resulting precipitate was filtered and dried under vacuum for about 16 h at about 60° C. to provide the title compound (0.033 g, 14%) as a white solid: LC/MS (Table 1, Method a) Rt=1.76 min; MS m/z: 364.1 (M+H)+.

後処理

  1. customprepared
  2. customThe MeOH was evaporated
  3. additionDCM (5 mL) was added
  4. customevaporated
  5. dissolutionThe resulting solid was dissolved in 1M TBAF in THF (5 mL)
  6. stirringto stir for about 30 min
  7. customThe THF was evaporated
  8. customthe crude material was purified by reverse phase HPLC (Table 1, Method f)
  9. additionThe fractions containing product
  10. concentrationwere concentrated under reduced pressure
  11. filtrationthe resulting precipitate was filtered
  12. customdried under vacuum for about 16 h at about 60° C.

出典と根拠

ORDレコード
ord-6e0462027c774273961b3dfd0c73820d
出典データセット
uspto-grants-2010_09
特許番号
US07790741B2

反応ノート

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