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N,N-Diethylethylenediamine → N-{[3-({[2-(diethylamino)ethyl]amino}carbonyl)phenyl](methyl)oxido--sulfanylidene}-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinamide

HRID 607444
ノート
印刷プレビュー

反応式

HRID 607444 の反応式
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([C:16]#[C:17][C:18]3[CH:19]=[C:20]([C:24]([N:26]=[S:27]([C:30]4[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=4)[C:33](O)=[O:34])([CH3:29])=[O:28])=[O:25])[CH:21]=[N:22][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][C:4]([CH3:39])=[N:3]1.[CH2:40]([N:42]([CH2:46][CH3:47])[CH2:43][CH2:44][NH2:45])[CH3:41].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:40]([N:42]([CH2:46][CH3:47])[CH2:43][CH2:44][NH:45][C:33]([C:32]1[CH:31]=[C:30]([S:27]([CH3:29])(=[O:28])=[N:26][C:24](=[O:25])[C:20]2[CH:19]=[C:18]([C:17]#[C:16][C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:39])[CH:5]=4)=[O:8])[CH:11]=3)[CH:23]=[N:22][CH:21]=2)[CH:38]=[CH:37][CH:36]=1)=[O:34])[CH3:41]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 60993N,N-DiethylethylenediamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576579273-[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]benzoic acid

生成物 1

HCID 57657887
N-{[3-({[2-(diethylamino)ethyl]amino}carbonyl)phenyl](methyl)oxido--sulfanylidene}-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-methylsulfonimidoyl]benzoic acid (52 mg, 0.096 mmol), 2-diethylaminoethylamine (0.016 ml, 0.115 mmol), and N,N-diisopropylethylamine (0.034 ml, 0.192 mmol) in 3.0 ml DMF at room temperature was added benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate (47 mg, 0.106 mmol). The reaction was stirred at room temperature for 1.5 hours, and then partitioned between EtOAc and dilute brine. The EtOAc layer was washed with saturated NaHCO3 solution, dilute brine, dried with anhydrous Na2SO4 and rotary evaporated. The yellow oil (combined 7 mg impure product from another lot) was chromatographed eluting with EtOAc/MeOH, then rechromatographed using a preparative TLC plate (eluted with (1:1:2.5) CHCl3:EtOAc:MeOH plus NH4OH) to give the title compound as a white solid foam (28 mg).

後処理

  1. custompartitioned between EtOAc and dilute brine
  2. washThe EtOAc layer was washed with saturated NaHCO3 solution, dilute brine
  3. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  4. customwas chromatographed
  5. washeluting with EtOAc/MeOH
  6. customrechromatographed
  7. washa preparative TLC plate (eluted with (1:1:2.5) CHCl3:EtOAc:MeOH plus NH4OH)

出典と根拠

ORDレコード
ord-d6188d6b21714b7dbcb0dea053a314ae
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915443B2

反応ノート

読み込み中…

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