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
4
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
Workup
- additionwas added
- concentrationthen concentrated under vacuum
- customThe residue which remained was triturated with aqueous sodium hydroxide
- filtrationfiltered
- washwashed with cold water
- customdried under vacuum
- customPurification by Gilson reverse phase HPLC
Sources & evidence
- ORD record
- ord-77f85e52aea24746b55b2aabea35b3c9
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495102B2
Reaction notes
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