(3-Aminopropoxy)(tert-butyl)dimethylsilane → N-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinecarboxamide
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][C:11](=[O:13])[NH:10][N:9]=2)=[C:4]([NH:14][CH:15]([CH3:17])[CH3:16])[CH:3]=1.[Si:18]([O:25][CH2:26][CH2:27][CH2:28][NH2:29])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(O)C>[Si:18]([O:25][CH2:26][CH2:27][CH2:28][NH:29][C:11]([NH:10][NH:9][C:8](=[O:12])[C:5]1[C:4]([NH:14][CH:15]([CH3:17])[CH3:16])=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1)=[O:13])([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:20])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2(3H)-one (49) (1.2 g, 4 mmol) and 3-((tert-butyldimethylsilyl)oxy)propan-1-amine (48) (7 mmol, 1.5 equiv.) were dissolved in ethanol (5 mL). Refluxed the reaction mixture at 90° C., overnight. The reaction mass was concentrated under reduced pressure to remove excess of solvent. The crude material obtained was taken to next step as such, without purification. LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 1.02 min; LCMS (ES-API), m/z 444.9 (M+H).
Workup
- customovernight
- concentrationThe reaction mass was concentrated under reduced pressure
- customto remove excess of solvent
Sources & evidence
- ORD record
- ord-66538a930e2743f2b68cac6417123973
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242976B2
Reaction notes
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