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

HRID 1772686Notes

Reaction equation

HRID 1772686 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[CH:13]=[C:14]([CH2:16][O:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=[C:11]3[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:9][CH:8]=2)[CH:2]=1.[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[CH:13]=[C:14]([CH2:16][O:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=[C:11]3[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:9][CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 863457682-[[8-(4-Morpholinyl)-5-(3-pyridinyl)imidazo[1,2-a]pyrazin-2-yl]methoxy]quinoline

Product 1

HCID 863457674-(5-(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 46a (90.0 mg, 0.205 mmol) in DCM (2 mL) was added a solution of methanesulfonic acid as a 1 M DCM solution (0.205 mL, 0.205 mmol). The reaction mixture was stirred at rt for 30 min and concentrated under reduced pressure to obtain the title compound 129. 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.81 (s, 6H), 3.92-4.03 (m, 4H), 4.57 (br. s., 4H), 5.78 (s, 2H), 7.18 (d, J=9.0 Hz, 1H), 7.47-7.56 (m, 1H), 7.70 (s, 1H), 7.75 (td, J=7.8, 1.3 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.94 (d, J=8.3 Hz, 1H), 8.01 (dd, J=8.1, 5.6 Hz, 1H), 8.18 (s, 1H), 8.27 (d, J=8.8 Hz, 1H), 8.54-8.62 (m, 1H), 8.90-8.97 (m, 1H), 9.16 (d, J=1.7 Hz, 1H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C25H22N6O2: 439.1 (M+H). Found 439.1.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b9128546ace445caab2633d75b3424e
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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