Dibutyltin oxide → HCID 178505985, compound
Reaction equation
C([Sn](CCCC)=O)CCC.[Cl:11][C:12]1[CH:13]=[C:14]2[C:20]([C:21]3[N:26]=[C:25]([NH:27][C@H:28]4[CH2:33][CH2:32][CH2:31][C@@H:30]([C:34]#[N:35])[CH2:29]4)[C:24]([F:36])=[CH:23][N:22]=3)=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1.[N:37]([Si](C)(C)C)=[N+:38]=[N-:39]>C1(C)C=CC=CC=1>[NH:37]1[C:34]([C@@H:30]2[CH2:31][CH2:32][CH2:33][C@H:28]([NH:27][C:25]3[C:24]([F:36])=[CH:23][N:22]=[C:21]([C:20]4[C:14]5[C:15](=[N:16][CH:17]=[C:12]([Cl:11])[CH:13]=5)[NH:18][CH:19]=4)[N:26]=3)[CH2:29]2)=[N:35][N:39]=[N:38]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A suspension of dibutyl(oxo)tin (0.016 g, 0.064 mmol) and (1R,3S)-3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]cyclohexane-carbonitrile (54c) (0.043 g, 0.107 mmol) in toluene (3 mL) was treated with azido(trimethyl)silane (0.200 mL, 1.507 mmol). The mixture was heated in a sealed tube at 120° C. overnight. The mixture was absorbed onto silica-gel and purified by silica gel chromatography (25-50% gradient of 20% MeOH:DCM containing 0.5% AcOH modifier). The combined fractions were concentrated to dryness to give a residue that was triturated with ether then dried under vacuum at 45° C. to afford 44 mg of a yellow solid.
Workup
- customThe mixture was absorbed onto silica-gel
- custompurified by silica gel chromatography (25-50% gradient of 20% MeOH:DCM containing 0.5% AcOH modifier)
- concentrationThe combined fractions were concentrated to dryness
- customto give a residue that
- customwas triturated with ether
- customthen dried under vacuum at 45° C.
Sources & evidence
- ORD record
- ord-ad904b61d269454288b16bbab9bbfab0
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345708B2
Reaction notes
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