Diisopropylethylamine → HCID 67194128, 화합물

HRID 551291

반응식

HRID 551291 반응식
[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

참가 물질

6

반응물 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

생성물 1

HCID 67194128HCID 67194128, 화합물수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ac3ec2b55b6a4f5bb096505160cd6c1c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947684B2

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