Water → HCID 69020706、化合物

HRID 229856ノート

反応式

HRID 229856 の反応式
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:18]([OH:20])=O.CN(C(ON1[N:37]=[N:36][C:31]2C=[CH:33][CH:34]=[CH:35][C:30]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NN1CCCCC1.O>CN(C=O)C>[N:36]1([NH:37][C:18]([C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([O:13][C:14]([F:15])([F:17])[F:16])=[CH:11][CH:12]=3)[NH:6][C:2]=2[CH3:1])=[O:20])[CH2:33][CH2:34][CH2:35][CH2:30][CH2:31]1

参加物

6

反応物 4

HCID 962WaterHCID 166581-AminopiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 534044015-Methyl-2-[4-(trifluoromethoxy)phenyl]-1H-imidazole-4-carboxylic acid

生成物 1

HCID 69020706HCID 69020706、化合物収率 89.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 1 g of 5-methyl-2-(4-trifluoromethoxy-phenyl)-1H-imidazole-4-carboxylic acid in 50 ml of DMF was added 1.12 g of TBTU and 3.0 ml of Hünigs' base and the reaction mixture was stirred for 1 minute. Then 0.38 ml of 1-aminopiperidine (as R1R2NH) was added and the reaction mixture was stirred for 4.5 hour at room temperature. After such time the reaction mixture was poured onto 250 ml of water and extracted with ethyl acetate (2×200 ml). The combined organic extracts were then washed with water (2×100 ml) and brine (50 ml), dried (MgSO4) and after filtration, concentrated in vacuo to yield an oil which crystallized during concentration. The residue (about 30 ml volume) was then treated with heptane (200 ml), the solid was filtered and dried to yield 1.15 g of the title compound, MS (ISP) 369.0 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred for 4.5 hour at room temperature
  2. extractionextracted with ethyl acetate (2×200 ml)
  3. washThe combined organic extracts were then washed with water (2×100 ml) and brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationafter filtration
  6. concentrationconcentrated in vacuo
  7. customto yield an oil which
  8. customcrystallized during concentration
  9. additionThe residue (about 30 ml volume) was then treated with heptane (200 ml)
  10. filtrationthe solid was filtered
  11. customdried

出典と根拠

ORDレコード
ord-651cc71e95d44cc99a19c6e2bfd581f8
出典データセット
uspto-grants-2009_07
特許番号
US07563910B2

反応ノート

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