Methanesulfonyl chloride → 6-(4-Methoxybenzyl)-9-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926120ノート

反応式

HRID 926120 の反応式
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[CH:17][C:12]=3[C:11]3=[N:25][CH:26]=[N:27][N:10]3[C:9]2=[O:28])=[CH:5][CH:4]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH2:18][N:19]4[CH2:24][CH2:23][N:22]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:21][CH2:20]4)=[CH:17][C:12]=3[C:11]3=[N:25][CH:26]=[N:27][N:10]3[C:9]2=[O:28])=[CH:29][CH:30]=1

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 1181350826-(4-Methoxybenzyl)-9-(piperazin-1-ylmethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5 (6H)-one

生成物 1

HCID 1181154846-(4-Methoxybenzyl)-9-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one収率 39.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

6-(4-Methoxybenzyl)-9-(piperazin-1-ylmethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 65, 34 mg, 0.09 mmol), ACN (1 mL), TEA (75 μl, 0.53 mmol), and methane sulfonyl chloride (50 mg, 0.44 mmol) were combined and the mixture was stirred for 4 h. The reaction was filtered through a plug of C18. Purification (HPLC, 10-70% ACN in water) afforded the title compound (17 mg, 33%) as a white solid. 1H NMR (400 MHz, CDCl3 and DMSO-d6) δ 2.48 (d, J=1.63 Hz, 2H), 2.76 (d, J=2.26 Hz, 3H), 3.09 (br s, 4H), 3.54 (br s, 4H), 3.65 (d, J=2.51 Hz, 3H), 4.21 (br s, 2H), 5.63 (d, J=1.76 Hz, 2H), 6.72 (dd, J=8.78, 2.26 Hz, 2H), 7.47 (dd, J=8.66, 2.38 Hz, 2H), 8.26 (d, J=2.38 Hz, 1H), 8.85 (br s, 1H), 9.00 (br s, 1H). [M+H]=484.2.

後処理

  1. filtrationThe reaction was filtered through a plug of C18
  2. customPurification (HPLC, 10-70% ACN in water)

出典と根拠

ORDレコード
ord-69db1d2fdb654c358dd9e733a81bc6ed
出典データセット
uspto-grants-2016_03
特許番号
US09284335B2

反応ノート

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