Sodium Azide → HCID 24764832, compound

HRID 1255112Notes

Reaction equation

HRID 1255112 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:24])[C:16]3[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=3[F:23])=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[N-:25]=[N+:26]=[N-:27].[Na+].Cl.[CH2:30]([NH+](CC)CC)C>CN(C=O)C.C(Cl)Cl>[F:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([F:23])[C:16]=1[C:15]([NH:14][C:12]1[S:13][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]3[N:25]=[N:26][N:27]([CH3:30])[N:2]=3)[CH:4]=2)=[CH:10][N:11]=1)=[O:24]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 21900368Triethylammonium hydrochlorideHCID 24764831HCID 24764831, compound

Product 1

HCID 24764832HCID 24764832, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Compound 6 (50 mg, 0.15 mmol), sodium azide (52 mg, 0.75 mmol), triethylammonium hydrochloride (21 mg, 0.15 mmol) in DMF (1 mL) was heated to 110° C. overnight. The mixture was cooled to room temperature, diluted with CH2Cl2. The mixture was eluted through a plug of silica (initially with CH2Cl2, then with 1:9, MeOH: CH2Cl2) provided the crude tetrazole upon solvent removal. Methylation of the crude tetrazole was accomplished by treating the residue with a freshly prepared solution of CH2N2 in ether. The reaction mixture was concentrated under reduced pressure. The residue was purified on silica gel to give Compound 7 (20 mg)

Workup

  1. washThe mixture was eluted through a plug of silica (initially with CH2Cl2
  2. customwith 1:9, MeOH: CH2Cl2) provided the crude tetrazole
  3. customupon solvent removal
  4. additionby treating the residue with a freshly prepared solution of CH2N2 in ether
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-71e80fe917ff4344b01cc6883db0e9b0
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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