Sodium Azide → HCID 24883024, compound

HRID 1927241Notes

Reaction equation

HRID 1927241 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[CH:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].I[C:23]1[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=1.CN[C@H]1CCCC[C@@H]1NC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[Cu]I.C(OCC)(=O)C.O.CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]2[N:18]=[N:19][N:20]([C:23]3[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:17]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 5

HCID 33557Sodium AzideHCID 27631512-Amino-3-iodopyridineHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 23667548Sodium AscorbateHCID 592553841-(Benzyloxy)-4-(prop-2-yn-1-yl)benzene

Product 1

HCID 24883024HCID 24883024, compoundYield 8.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of DMSO (5.0 mL), water (1.0 mL) and 1-benzyloxy-4-prop-2-ynyl-benzene (50 mg) described in Manufacturing Example 12-2 were added sodium azide (16 mg), 3-iodopyridin-2-ylamine (50 mg) described in Manufacturing Example 1-2, copper(I) iodide (4.3 mg), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (CAS No. 87583-89-9; 4.8 mg), and sodium ascorbate (4.5 mg), which was stirred for 3 hours at 60° C., and then, which was stirred for 2 days at room temperature. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered, and then the filtrate was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the titled compound (6.7 mg).

Workup

  1. extractionthe organic layer was extracted
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1)

Sources & evidence

ORD record
ord-9ceefbac87f64bf5b88c125177ce6f57
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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