Triethylamine → methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester

HRID 1887422ノート

反応式

HRID 1887422 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:36])[CH:31]=[CH:32][CH2:33][CH2:34][OH:35])[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:36])[CH:31]=[CH:32][CH2:33][CH2:34][O:35][S:45]([CH3:44])(=[O:47])=[O:46])[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 668770631-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenyl amino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-hydroxy-pent-2-en-1-one

生成物 1

HCID 72332921methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a 250 ml rb flask were placed 1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenyl amino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-hydroxy-pent-2-en-1-one (1.00 g, 1.91 mmol) in THF (80 ml) and to the solution was added triethylamine (0.58 g, 5.74 mmol) (0.80 ml) followed by methanesulfonyl chloride (0.54 g, 4.79 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. THF was evaporated and to the residue was added water and small amount of methyl alcohol, sonicated. The precipitated off-white solid was filtered, washed with methyl alcohol and dried to provide 0.63 g of off-white solid. (55%) 1H-NMR (DMSO-d6) δ 8.601-8.585 (m, 1H), 8.394 (s, 1H), 8.196 (s, 1H), 7.906-7.864 (m, 1H), 7.769 (s, 1H), 7.584-7.564 (d, 1H), 7.523-7.501 (d, 1H), 7.388-7.357 (m, 1H), 7.239-7.216 (d, 1H), 6.765-6.703 (m, 2H), 5.280 (s, 2H), 4.957 (s, 1H), 4.843 (s, 1H), 4.366-4.337 (m, 2H), 3.940-3.860 (m, 2H), 3.255-3.189 (m, 6H), 2.655-2.626 (m, 2H). MS m/e 600.0 (M+H), RT=2.78 min

後処理

  1. customIn a 250 ml rb flask were placed
  2. customTHF was evaporated and to the residue
  3. additionwas added water and small amount of methyl alcohol
  4. customsonicated
  5. filtrationThe precipitated off-white solid was filtered
  6. washwashed with methyl alcohol
  7. customdried

出典と根拠

ORDレコード
ord-a48176950cd540c2964d706c26e03984
出典データセット
uspto-grants-2013_08
特許番号
US08501755B2

反応ノート

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