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 926120Notes

Reaction equation

HRID 926120 reaction equation
[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

Participants

4

Reactant 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

Product 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)-oneYield 39.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-69db1d2fdb654c358dd9e733a81bc6ed
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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