Potassium Carbonate → 3-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)-N,N-dimethylpropan-1-amine

HRID 1642564

Reaction equation

[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH3:27][N:28]([CH3:43])[CH2:29][CH2:30][CH2:31]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:31][CH2:30][CH2:29][N:28]([CH3:43])[CH3:27])=[C:17]3[C:13]=2[C:14]2[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

Conditions

Temperature: 200 °C

Procedure

A 5 mL microwave vial was charged with Compound 157 (290 mg, 0.79 mmol), 3-(dimethylamino)propyl-4-methylbenzenesulfonate (224 mg, 0.87 mmol), potassium carbonate (218 mg, 1.58 mmol) and 2 mL of anhydrous DMF, under nitrogen atmosphere. The reaction mixture was heated at 200° C. for 30 min. in microwave with high absorption. The reaction was quenched with addition of water, and the solid precipitate out was collected by filtration and purified through preparative HPLC to provide title compound (1438 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.33 Hz, 3 H) 1.99 (qd, J=6.61, 6.44 Hz, 2 H) 2.20 (s, 6 H) 2.26 (s, 3 H) 2.53-2.56 (m, 2 H) 3.41 (q, J=7.33 Hz, 2 H) 4.25 (t, J=6.19 Hz, 2 H) 7.05-7.09 (m, 1 H) 7.11-7.14 (m, 1 H) 7.54 (d, J=1.52 Hz, 1 H) 7.85 (t, J=7.83 Hz, 1 H) 7.98 (t, J=6.95 Hz, 2 H) 8.06-8.08 (m, 1 H) 8.27 (d, J=1.77 Hz, 1 H) 12.13 (s, 1 H); [M+H] calc'd for C25H30N3O3S, 452.2; found, 452.4.

Workup

customThe reaction was quenched with addition of water
filtrationthe solid precipitate out was collected by filtration
custompurified through preparative HPLC

Sources & evidence

ORD record: ord-878974a300dd43f9bdeaaaf55efab833
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Linked notes

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