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N-isopropyl-6-(tributylstannyl)pyrazin-2-amine → 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

HRID 634257
ノート
印刷プレビュー

反応式

HRID 634257 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:15][N:14]=[C:13]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[N:12]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[CH:36]([NH:39][C:40]1[CH:45]=[N:44][CH:43]=[C:42]([Sn](CCCC)(CCCC)CCCC)[N:41]=1)([CH3:38])[CH3:37]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:36]([NH:39][C:40]1[N:41]=[C:42]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[S:15][N:14]=[C:13]([NH:16][CH2:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=5)[N:12]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=3)(=[O:27])=[O:28])[CH:3]=2)[CH:43]=[N:44][CH:45]=1)([CH3:38])[CH3:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 68328197N-isopropyl-6-(tributylstannyl)pyrazin-2-amineHCID 683287145-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine

生成物 1

HCID 683286605-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine収率 63.5%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A solution of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.78 g, 1.26 mmol) and N-isopropyl-6-(tributylstannyl)pyrazin-2-amine ((0.65 g, 1.52 mmol) in DMF (8 mL) was purged with argon for 15 min. To the above mixture, CuI (0.289 g, 1.52 mmol) and Pd(PPh3)4 (0.146 g, 0.126 mmol) was added and argon gas was purged for another 15 min. The reaction was heated at 90° C. for 1 h, then cooled to RT. The mixture was treated with ice cold H2O to obtain off brown precipitate. The precipitate was filtered and washed with H2O and dried. The crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether) to give 5-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,2,4-thiadiazol-3-amine (0.5 g, 63.5%) as an off brown solid. MS (ESI, pos. ion) m/z: 626.2 (M+1); 1H-NMR (300 MHz, DMSO-d6): δ 9.02 (brs, 1H), 8.70 (s, 1H), 8.18-8.16 (m, 1H), 7.99 (m, 2H), 7.65-7.75 (m, 3H), 7.44-7.40 (m, 3H), 7.30-7.28 (m, 2H), 1.70-7.68 (m, 1H), 6.88 (m, 1H), 4.42 (m, 2H), 3.71 (s, 3H), 2.31 (s, 3H), 1.56 (m, 6H).

後処理

  1. customargon gas was purged for another 15 min
  2. temperaturecooled to RT
  3. additionThe mixture was treated with ice cold H2O
  4. customto obtain off brown precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with H2O
  7. customdried
  8. customThe crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-3363c8dc7ff94e61a675bc99461074e1
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321756B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート