Trifluoroacetic acid → 4-(5-((1,1-Dioxidohexahydro-5H-isothiazolo[2,3-A]pyrazin-5-YL)methyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1812437Notes

Reaction equation

HRID 1812437 reaction equation
[O:1]=[S:2]1(=[O:54])[N:6]2[CH2:7][CH2:8][N:9]([CH2:11][C:12]3[CH:13]=[C:14]([C:28]4[N:33]=[C:32]([CH3:34])[N:31]=[C:30]([N:35](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)[N:29]=4)[C:15]([NH:18][C:19]4[CH:20]=[N:21][C:22]([O:26][CH3:27])=[C:23]([F:25])[CH:24]=4)=[N:16][CH:17]=3)[CH2:10][CH:5]2[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>>[O:54]=[S:2]1(=[O:1])[N:6]2[CH2:7][CH2:8][N:9]([CH2:11][C:12]3[CH:13]=[C:14]([C:28]4[N:33]=[C:32]([CH3:34])[N:31]=[C:30]([NH2:35])[N:29]=4)[C:15]([NH:18][C:19]4[CH:20]=[N:21][C:22]([O:26][CH3:27])=[C:23]([F:25])[CH:24]=4)=[N:16][CH:17]=3)[CH2:10][CH:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 666116654-(5-((1,1-dioxidohexahydro-5H-isothiazolo[2,3-a]pyrazin-5-yl)methyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 497858314-(5-((1,1-Dioxidohexahydro-5H-isothiazolo[2,3-A]pyrazin-5-YL)methyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine

Procedure

The title compound was prepared from 4-(5-((1,1-dioxidohexahydro-5H-isothiazolo[2,3-a]pyrazin-5-yl)methyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine via the similar deprotection protocol as described previously in Example 178, Step 4, using trifluoroacetic acid and trifluoromethanesulfonic acid and isolated (61 mg, 30%) as a yellow solid. m/z (ESI, +ve ion) 516 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.95 (s, 1H) 8.73 (d, J=2.15 Hz, 1H) 8.42 (d, J=2.15 Hz, 1H) 8.37 (dd, J=12.81, 2.05 Hz, 1H) 8.26 (d, J=2.15 Hz, 1H) 7.91 (br. s., 1H) 7.76 (br. s., 1H) 3.93 (s, 3H) 3.45-3.62 (m, 1H) 3.00-3.30 (m, 5H) 2.80-3.00 (m, 2H) 2.62-2.74 (m, 1H) 2.44 (s, 3H) 2.23-2.36 (m, 1H) 2.06-2.16 (m, 1H) 1.81-1.96 (m, 2H).

Workup

  1. customisolated (61 mg, 30%) as a yellow solid

Sources & evidence

ORD record
ord-9fd657789af845ce90f2692ba9802650
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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