Methanesulfonic Acid → 4-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine methane sulfonic acid salt

HRID 1772689Notes

Reaction equation

HRID 1772689 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:18]4[CH:19]=[C:20]([CH2:22][O:23][C:24]5[CH:33]=[CH:32][C:31]6[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=6)[N:25]=5)[N:21]=[C:17]4[C:16]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:40][S:41]([OH:44])(=[O:43])=[O:42]>C(Cl)Cl>[CH3:40][S:41]([OH:44])(=[O:43])=[O:42].[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[N:18]4[CH:19]=[C:20]([CH2:22][O:23][C:24]5[CH:33]=[CH:32][C:31]6[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=6)[N:25]=5)[N:21]=[C:17]4[C:16]([N:34]4[CH2:35][CH2:36][O:37][CH2:38][CH2:39]4)=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 863457724-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 863457714-(5-(6-(Piperazin-1-yl)pyridin-3-yl)-2-((quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine methane sulfonic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 47b (90.0 mg, 0.172 mmol) in DCM (2 mL) was added a solution of methanesulfonic acid as a 1 M DCM solution (0.172 mL, 0.172 mmol). The reaction mixture was stirred at rt for 30 min and then concentrated under reduced pressure to obtain the title compound 126. 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.71 (s, 6H), 3.19-3.26 (m, 4H), 3.85-3.91 (m, 8H), 4.43 (br. s., 4H), 5.60 (s, 2H), 6.83 (d, J=9.0 Hz, 1H), 6.88 (d, J=8.8 Hz, 1H), 7.32 (s, 1H), 7.33-7.38 (m, 1H), 7.56 (td, J=7.7, 1.5 Hz, 1H), 7.63-7.70 (m, 2H), 7.73 (d, J=8.6 Hz, 1H), 7.79 (s, 1H), 7.98 (d, J=8.8 Hz, 1H), 8.26 (d, J=2.4 Hz, 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C29H30N8O2: 523.2 (M+H). Found 523.3.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1da209d23b4c4a63ae4bf5505e3ca713
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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