Potassium Carbonate → HCID 57502416, compound

HRID 1926637Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]5)[CH:19]=[N:18][CH:17]=4)=[CH:14][N:13](S(C4C=CC=CC=4)(=O)=O)[C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]5)[CH:19]=[N:18][CH:17]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of tert-butyl 4-{6-[5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}piperazine-1-carboxylate (0.077 g, 0.13 mmol) in MeOH (1.3 ml) was added potassium carbonate (0.053 g, 0.34 mmol). The reaction mixture was stirred at 50° C. for 1 hour, then at room temperature for 16 hours. The reaction mixture was diluted with MeOH (10 mL) and DCM (10 mL), silica gel was added, and concentrated to a crude residue. The crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient, followed by MeOH/DCM gradient) to afford tert-butyl 4-{6-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrazin-2-yl}piperazine-1-carboxylate as a white solid. LRMS calculated for C24H28N8O2 [M+H]+, 461.2; found 461.2.

Workup

waitat room temperature for 16 hours
additionwas added
concentrationconcentrated to a crude residue
customThe crude residue was purified by silica gel chromatography (EtOAc/Hexanes gradient, followed by MeOH/DCM gradient)

Sources & evidence

ORD record: ord-8c67292e57e7419db8c3c550d1fddc04
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183245B2

Reaction notes

Loading…