Triethylamine hydrochloride → HCID 59004503, compound

HRID 1255114Notes

Reaction equation

HRID 1255114 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][C:10]=2[CH3:25])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C([N:29]([CH2:32]C)CC)C.[N:34]([Si](C)(C)C)=[N+:35]=[N-]>CN(C=O)C.C(Cl)Cl>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[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:34]=[N:35][N:29]([CH3:32])[N:2]=3)[CH:4]=2)=[C:10]([CH3:25])[N:11]=1)=[O:24]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 78378AzidotrimethylsilaneHCID 59004550HCID 59004550, compound

Product 1

HCID 59004503HCID 59004503, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-[5-(3-Cyano-phenyl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide (0.23 mmol), and triethylamine hydrochloride (32.0 mg, 0.23 mmol) in DMF (1 mL) was added excess azidotrimethylsilane (0.20 mL). The mixture was sealed and heated to 100° C. overnight, cooled to room temperature. The mixture was diluted with CH2Cl2. The resulting solution was eluted through a short plug of silica (eluted first with CH2Cl2 then with MeOH). The polar portion was concentrated to give the tetrazole product, which was directly methylated with a freshly prepared solution of CH2N2 in ether. Upon solvent removal, the title compound was obtained as a white solid.

Workup

  1. customThe mixture was sealed
  2. temperaturecooled to room temperature
  3. washThe resulting solution was eluted through a short plug of silica (
  4. washeluted first with CH2Cl2
  5. concentrationThe polar portion was concentrated

Sources & evidence

ORD record
ord-8cc102356b53435eb5fe8cfb11edff05
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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