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Cesium carbonate → 4-(Benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-one

HRID 2387478
Notes
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Reaction equation

HRID 2387478 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[N:19]=[CH:18]3)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 767274-(2-Chloroethyl)morpholineHCID 576255174-(benzyloxy)-1-(1H-indazol-5-yl)pyridin-2(1H)-one

Product 1

HCID 250576454-(Benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-oneYield 7.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Procedure

To a solution of 4-(benzyloxy)-1-(1H-indazol-5-yl)pyridin-2(1H)-one (0.362 g, 1.14 mmol) in DMSO (1.5 mL) was added 4-(2-chloroethyl)morpholine (0.466 g, 2.50 mmol) and Cs2CO3 (1.85 g, 5.67 mmol). After stirring at ambient temperature for 5.5 h, the reaction mixture was diluted with H2O (10 mL) and extracted with EtOAc (3×40 mL). The organics were washed with brine (2×25 mL), dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) followed by preparative HPLC (Phenomenex Luna C18 (2), 250.0×50.0 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) yielded the title compound (37.3 mg, 7%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 8.02 (d, J=1.0 Hz, 1H), 7.66 (d, J=1.5 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 7.43-7.38 (m, 6H), 7.29 (d, J=7.5 Hz, 1H), 6.09-6.06 (m, 2H), 5.06 (s, 2H), 4.53 (t, J=7.0 Hz, 2H), 3.68 (t, J=4.5 Hz, 4H), 2.88 (t, J=6.5 Hz, 2H) 2.52 (t, J=4.5 Hz, 4H); ESI MS m/z 431 [M+H]+; HPLC (Method A) 98.9% (AUC), tR=14.0 min.

Workup

  1. extractionextracted with EtOAc (3×40 mL)
  2. washThe organics were washed with brine (2×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100)

Sources & evidence

ORD record
ord-c6d5784dddf145c0b9c7d9711f44b473
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268868B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes