Water → HCID 178525674, compound
Reaction equation
[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:3]=1[C:4]([N:6]1[CH2:11][C@@H:10]2[CH2:12][C@H:7]1[CH2:8][N:9]2[CH2:13][C:14]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[CH:24][N:23](COCC[Si](C)(C)C)[N:22]=2)[CH:17]=[N:16][CH:15]=1)=[O:5].O.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:3]=1[C:4]([N:6]1[CH2:11][C@@H:10]2[CH2:12][C@H:7]1[CH2:8][N:9]2[CH2:13][C:14]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[CH:24][NH:23][N:22]=2)[CH:17]=[N:16][CH:15]=1)=[O:5]Participants
4
Procedure
19 mg of 6-(((1S,4S)-5-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]hept-2-yl)methyl)-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrazine-2-amine was dissolved in 1 ml of trifluoroacetic acid and 0.1 ml of water followed by stirring at room temperature for 15 hours. The reaction solution was concentrated in vacuo, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate, water and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=5/1) to give the title compound.
Workup
- concentrationThe reaction solution was concentrated in vacuo
- additiondiluted with ethyl acetate
- washwashed with saturated sodium bicarbonate, water and brine
- dry with materialThe resulting organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=5/1)
Sources & evidence
- ORD record
- ord-c5d911d8eb174cac90c552273352b252
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101621B2
Reaction notes
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