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

HRID 1670556
Notes
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Reaction equation

HRID 1670556 reaction equation
[CH2:1]([C:3]1[NH:7][C:6](=[S:8])[NH:5][N:4]=1)[CH3:2].[H-].[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][C:22]2[C:25]([CH2:30]Cl)=[C:26]([Cl:29])[CH:27]=[CH:28][C:21]=2[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][C:22]2[C:25]([CH2:30][S:8][C:6]3[NH:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=3)=[C:26]([Cl:29])[CH:27]=[CH:28][C:21]=2[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 1784380535-ethyl-1H-1,2,4-triazole-3-thiol

Product 1

HCID 1784379773-tert-butoxycarbonyl-7-chloro-6-(5-ethyl-1H-1,3,4-triazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 73%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

Dissolve 5-ethyl-1H-1,3,4-triazole-2-thione (92 mg, 0.71 mmol) in anhydrous DMF (5 mL). Add sodium hydride (40 mg, 0.925 mmol, 60% dispersion in mineral oil) at room temperature under a nitrogen atmosphere and stir for 10 min. Add a solution of 3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (210 mg, 0.65 mmol) in anhydrous DMF (5 mL) at room temperature over 3 min and stir under nitrogen for 18 h. Quench with saturated aqueous NH4Cl (ca. 1 mL) and pour into water (100 mL). Extract the aqueous phase with EtOAc (3×25 mL) and wash the combined organic extracts with brine. Dry the organic solution over Na2SO4, filter and concentrate in vacuo to obtain crude 3-tert-butoxycarbonyl-7-chloro-6-(5-ethyl-1H-1,3,4-triazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (200 mg, 73%) suitable for use without further purification. MS (ES+) m/z: 423 (M+H)+.

Workup

  1. customQuench with saturated aqueous NH4Cl (ca. 1 mL)
  2. additionpour into water (100 mL)
  3. extractionExtract the aqueous phase with EtOAc (3×25 mL)
  4. washwash the combined organic extracts with brine
  5. dry with materialDry the organic solution over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-3285e335dd014192a1878bb78624ca11
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994163B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes