1-Hydroxybenzotriazole → HCID 59483860、化合物

HRID 1808389ノート

反応式

HRID 1808389 の反応式
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:32][C:33]1[S:37][C:36]([C:38](Cl)=[O:39])=[CH:35][CH:34]=1.[N:41]1[CH:46]=[CH:45][C:44]([N:47]2[CH2:75][CH2:74][C:50]3([CH2:55][CH2:54][N:53]([C:56]([C:58]4[N:59]=[C:60]5[CH2:65][N:64](C(OC(C)(C)C)=O)[CH2:63][CH2:62][N:61]5[CH:73]=4)=[O:57])[CH2:52][CH2:51]3)[CH2:49][CH2:48]2)=[CH:43][CH:42]=1>C(Cl)Cl>[Cl:32][C:33]1[S:37][C:36]([C:38]([N:64]2[CH2:63][CH2:62][N:61]3[CH:73]=[C:58]([C:56]([N:53]4[CH2:52][CH2:51][C:50]5([CH2:74][CH2:75][N:47]([C:44]6[CH:43]=[CH:42][N:41]=[CH:46][CH:45]=6)[CH2:48][CH2:49]5)[CH2:55][CH2:54]4)=[O:57])[N:59]=[C:60]3[CH2:65]2)=[O:39])=[CH:35][CH:34]=1

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59483777HCID 59483777、化合物

生成物 1

HCID 59483860HCID 59483860、化合物収率 11%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

EDCl (1.29 mmol, 1.5 equiv.), HOBt (1.29 mmol, 1.5 equiv.) and DIPEA (3.44 mmol, 4 equiv.) were added at 0° C. to a solution of 5-chlorothiophene-2-carbonyl chloride (0.86 mmol, 1.0 equiv.) in DCM (20 ml), and the mixture was stirred for 30 min. A solution of tert-butyl 2-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carbonyl)-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (0.86 mmol, 1.0 equiv.) in DCM (5 ml) was then added, the ice bath was removed, and stirring was carried out for 16 h at 25° C. The reaction mixture was diluted with dichloromethane (100 ml) and washed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (8% methanol in DCM) and the desired product was thus obtained in the form of a white solid. Yield: 11%. MS, Rt=2.7 min; m/z=525.2 [MH]+

後処理

  1. customthe ice bath was removed
  2. stirringstirring
  3. waitwas carried out for 16 h at 25° C
  4. additionThe reaction mixture was diluted with dichloromethane (100 ml)
  5. washwashed with sat. sodium carbonate solution (65 ml), sat. ammonium chloride solution (65 ml), water (50 ml) and sat. sodium chloride solution (50 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (8% methanol in DCM)

出典と根拠

ORDレコード
ord-70aa3c10100c4a61acdba52889d4b8b7
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

反応ノート

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