Diisopropylethylamine → 5-Bromo-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

HRID 598228ノート

反応式

HRID 598228 の反応式
[Br:1][C:2]1[C:3]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:52][CH2:53][C:54]([CH3:59])([CH:56]1[CH2:58][CH2:57]1)[OH:55]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([NH:52][CH2:53][C:54]([CH:56]1[CH2:58][CH2:57]1)([OH:55])[CH3:59])=[O:9]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 211096921-Amino-2-cyclopropylpropan-2-olHCID 863463205-Bromo-6-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)nicotinic acid

生成物 1

HCID 866347985-Bromo-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide収率 27.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Bromo-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinic acid (1.1 g, 3.0 mmol) was dissolved in DMF (25 mL). To the solution was added TBTU (1.06 g, 3.3 mmol), N,N-diisopropylethyl amine (2.54 mL, 15 mmol) and α-(aminomethyl)-α-methyl-cyclopropanemethanol (0.38 g, 3.3 mmol). The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (20 mL), washed with sodium hydroxide solution (0.5 N) and brine. Organic phases were pooled, dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, heptane/ethyl acetate) to give the title compound (0.38 g) as a light yellow solid, MS (ISP) 462.9, 464.9 (M−H)+.

後処理

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (20 mL)
  3. washwashed with sodium hydroxide solution (0.5 N) and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-6402f0a619344f398036353ce5c2073e
出典データセット
uspto-grants-2011_03
特許番号
US07897621B2

反応ノート

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