Isopropanol → 4-(2-(6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,6-dimethyl-1,3,5-triazin-2-amine

HRID 1621613Notes

Reaction equation

HRID 1621613 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([C:18]3[N:23]=[C:22]([CH3:24])[N:21]=[C:20](SC)[N:19]=3)=[CH:16][C:15]([CH2:27][N:28]3[CH2:33][CH2:32][N:31]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:30][CH2:29]3)=[CH:14][N:13]=2)=[CH:7][CH:6]=1.CC(O)C>>[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([C:18]3[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:2][CH3:1])[N:19]=3)=[CH:16][C:15]([CH2:27][N:28]3[CH2:29][CH2:30][N:31]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:32][CH2:33]3)=[CH:14][N:13]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 6329MethylamineHCID 66599816N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-amine

Product 1

HCID 595483614-(2-(6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,6-dimethyl-1,3,5-triazin-2-amineYield 54.7%

Procedure

Methylamine was bubbled through a mixture of N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-amine (33 mg, 0.064 mmol) in IPA (1.50 mL, 19.47 mmol) for 15 min and then allowed to stand overnight. The resulting precipitate was collected by filtration and washed with a minimal amount of IPA to give 4-(2-(6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,6-dimethyl-1,3,5-triazin-2-amine (17.1 mg, 1.761 mmol, 54.7% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) mixture of rotamers δ 11.26-12.03 (m, 1H); 8.73 (d, J=13.69 Hz, 1H); 8.38-8.63 (m, 1H); 7.96-8.38 (m, 3H); 6.83 (d, J=8.41 Hz, 1H); 3.84 (br. s., 3H); 3.50 (d, J=12.72 Hz, 2H); 3.11 (br. s., 4H); 2.90-3.03 (m, 3H); 2.86 (br. s., 3H); 2.47-2.50 (m, 4H); 2.44 (br. s., 3H). m/z (ESI, +ve ion) 500.1 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with a minimal amount of IPA

Sources & evidence

ORD record
ord-026869113a76495eae6bab4f4f867b3c
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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