3-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 3-tert-butoxycarbonyl-7-chloro-6-(3H-[1,2,3]triazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1670557Notes

Reaction equation

HRID 1670557 reaction equation
[Na].[NH:2]1[C:6]([SH:7])=[CH:5][N:4]=[N:3]1.[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([CH2:27]Cl)=[C:23]([Cl:26])[CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CN(C=O)C>[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][C:19]2[C:22]([CH2:27][S:7][C:6]3[NH:2][N:3]=[N:4][CH:5]=3)=[C:23]([Cl:26])[CH:24]=[CH:25][C:18]=2[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 1785277431H-1,2,3-Triazole-4-thiol, monosodium salt

Product 1

HCID 1784515903-tert-butoxycarbonyl-7-chloro-6-(3H-[1,2,3]triazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Slurry 1H-[1,2,3]triazole-5-thiol sodium salt (465 mg, 3.78 mmol) in anhydrous DMF (20 mL). Add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.1 g, 3.4 mmol) in anhydrous DMF (10 mL) dropwise over 10 min under nitrogen. Stir at room temperature for 3 h. Quench by addition of saturated NH4Cl (100 mL). Extract with EtOAc (3×50 mL) and dry the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to obtain 3-tert-butoxycarbonyl-7-chloro-6-(3H-[1,2,3]triazol-4-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.2 g, 90%) as a yellow oil suitable for use without further purification.

Workup

  1. customQuench by addition of saturated NH4Cl (100 mL)
  2. extractionExtract with EtOAc (3×50 mL)
  3. dry with materialdry the combined organic extracts with water and brine
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-dfee4f2806b74f61989725607ab2cc1f
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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