Dimethylamine → Gsk-1070916

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[NH:19][C:20]([C:22]5[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:31])[CH3:30])[CH:23]=5)=[CH:21][C:14]=34)=[CH:11][N:10]([CH2:32][CH3:33])[N:9]=2)=[CH:4][CH:3]=1.[CH3:34][NH:35][CH3:36].[O:37]1[CH2:41]CCC1>>[CH3:31][N:29]([CH2:28][C:24]1[CH:23]=[C:22]([C:20]2[NH:19][C:15]3=[N:16][CH:17]=[CH:18][C:13]([C:12]4[C:8]([C:5]5[CH:4]=[CH:3][C:2]([NH:1][C:41](=[O:37])[N:35]([CH3:36])[CH3:34])=[CH:7][CH:6]=5)=[N:9][N:10]([CH2:32][CH3:33])[CH:11]=4)=[C:14]3[CH:21]=2)[CH:27]=[CH:26][CH:25]=1)[CH3:30]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran2×

HCID 689990183-[4-[3-(4-Aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl]-N,N-dimethylbenzenemethanamine

Product 1

HCID 46885626Gsk-1070916Yield 46%

Procedure

To a stirred solution of 4-[3-(4-aminophenyl)-1-ethyl-1H-pyrazol-4-yl]-2-[3-(dimethylaminomethyl)phenyl]-1H-pyrrolo[2,3-b]pyridine (1.0 mmol) in tetrahydrofuran (15 mL) was added p-nitrophenylchloroformate (1.1 mmol). After stirring for 1 h at room temperature a solution of 2.0 M dimethylamine in tetrahydrofuran (14 mmol) was added. The reaction was stirred an additional 1 h at room temperature then concentrated under vacuum. The residue which remained was triturated with aqueous sodium hydroxide, filtered, washed with cold water, and dried under vacuum. Purification by Gilson reverse phase HPLC afforded title compound as an off-white solid (46%). ESMS (M+H)+: 508.4