Diisopropylethylamine → HCID 67194128、化合物

HRID 551291

反応式

HRID 551291 の反応式
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:15]([OH:17])=O)[CH:12]=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:51]([C:53]1[CH:54]=[C:55]([N:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)[CH:56]=[CH:57][CH:58]=1)#[N:52]>CN(C)C=O>[C:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]([N:62]3[CH2:61][CH2:60][N:59]([C:55]4[CH:54]=[C:53]([CH:58]=[CH:57][CH:56]=4)[C:51]#[N:52])[CH2:64][CH2:63]3)=[O:17])[CH:12]=[N:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114809021-(3-Cyanophenyl)piperazine

生成物 1

HCID 67194128HCID 67194128、化合物収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.4 g, 1.8 mmol) in anhydrous dimethylformamide (3 ml) is treated with HATU (0.7 g, 1.8 mmol) and diisopropylethylamine (0.6 ml, 3.3 mmol). The reaction mixture is stirred 10 mins. at ambient temperature before being treated with a solution of 1-(3-cyanophenyl)piperazine (0.3 g, 1.6 mmol) in dimethylformamide (5 ml). The reaction mixture is stirred at ambient temperature for 18 hours, concentrated under vacuum and the residue partitioned between dichloromethane (2×40 ml) and saturated aqueous sodium bicarbonate (40 ml). The organic layer is dried (magnesium sulfate), concentrated under vacuum and the residue chromatographed on silica gel (ethyl acetate) to give the title compound as a yellow oil (0.33 g). 1H NMR (CDCl3, 500 MHz) δ8.82 (s, 1H), 8.61 (s, 1H), 7.90 (s, 1H), 7.58 (m, 2H), 7.39 (m, 4H), 7.16 (m, 3H), 3.95 (br m, 2H), 3.63 (br m, 2H), 3.30 (br m, 4H), EI MS M++H: 393.

後処理

  1. stirringThe reaction mixture is stirred at ambient temperature for 18 hours
  2. concentrationconcentrated under vacuum
  3. customthe residue partitioned between dichloromethane (2×40 ml) and saturated aqueous sodium bicarbonate (40 ml)
  4. dry with materialThe organic layer is dried (magnesium sulfate)
  5. concentrationconcentrated under vacuum
  6. customthe residue chromatographed on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-ac3ec2b55b6a4f5bb096505160cd6c1c
出典データセット
uspto-grants-2011_05
特許番号
US07947684B2

関連ノート

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