Potassium Carbonate → (S)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-hexanoic acid ethyl ester

HRID 2175165Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]([N:10]1[C:14]2=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=[C:13]2[NH:12][C:11]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2].C([O-])([O-])=O.[K+].[K+].[I-].[CH3:29][N:30]1[C:38]2[C:33](=[C:34]([CH3:39])[CH:35]=[CH:36][CH:37]=2)[C:32]([CH2:40][N+](C)(C)C)=[CH:31]1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]([N:10]1[C:14]2=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=[C:13]2[N:12]([CH2:40][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])[N:30]([CH3:29])[CH:31]=2)[C:11]1=[O:20])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-3-(5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-hexanoic acid ethyl ester (247 mg, 0.85 mmol) in DMF (5 mL) were added K2CO3 (234 mg, 1.7 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (438 mg, 1.27 mmol). The reaction mixture was heated to 60° C. for 48 hours. The reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 170 mg (45%) of the title compound. LCMS, M++1, m/z: 449.47.

Workup

washwashed with water (×4)
dry with materialThe organic phase was dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record: ord-9ec4544fc6064629b8b01bccc0b9201b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062056B2

Reaction notes

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