2,9-Dimethyl-1,10-phenanthroline → 2-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester

HRID 1366853ノート

反応式

HRID 1366853 の反応式
CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29](I)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[N:33]1([S:39]([C:42]2[CH:47]=[CH:46][C:45]([SH:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29]([S:48][C:45]2[CH:44]=[CH:43][C:42]([S:39]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)(=[O:40])=[O:41])=[CH:47][CH:46]=2)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

参加物

7

反応物 4

HCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 23676156Sodium t-butoxideHCID 57718193HCID 57718193、化合物HCID 577182904-(N-piperidinylsulfonyl)thiophenol

生成物 1

HCID 577182132-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester収率 56%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒

実験手順

Copper iodide (26 mg, 0.14 mmol) and neocuproine (29 mg, 0.14 mmol) were added to a stirred mixture of 2-amino-5-iodo-isonicotinic acid pentyl ester (450 mg, 1.35 mmol), 4-(piperidine-1-sulfonyl)-benzenethiol (449 mg, 1.49 mmol) and sodium t-butoxide (195 mg, 2.025 mmol) in toluene (10 ml) and the reaction was heated to reflux overnight. The reaction was cooled to room temperature, solids filtered off through celite and the filtrate concentrated under reduced pressure onto silica. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to afford 2-amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester as an orange solid (348 mg, 56%). 1H NMR (CDCl3): (1 H, s, py); 7.51 (2 H, d, Ar); 7.10 (2 H, d, Ar); 6.80 (1 H, s, py); 4.92 (2 H, br s, NH2); 4.14 (2 H, t, OCH2); 2.90 (4 H, m, 2×CH2N pip); 1.53 (6 H, m, OCH2CH2, 2×CH2 pip); 1.46 (2 H, m, CH2 pip); 1.24 (4 H, m, OCH2CH2CH2CHCH3); 0.80 (3 H, t, CH2CH3).

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationsolids filtered off through celite
  4. concentrationthe filtrate concentrated under reduced pressure onto silica
  5. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-e0fd27b96bd04625b6812936125c34ee
出典データセット
uspto-grants-2011_02
特許番号
US07893077B2

反応ノート

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