Nitrogen → HCID 24969711, compound

HRID 1157744Notes

Reaction equation

HRID 1157744 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([CH:12]([S:17][C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)=[C:20]([CH3:35])[CH:19]=2)[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][CH:11]=1)=[O:6])#[N:2].Cl.C(N(CC)CC)C.[N-:44]=[N+:45]=[N-:46].[Na+].N#N>C1(C)C=CC=CC=1>[N:2]1[NH:44][N:45]=[N:46][C:1]=1[CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([CH:12]([S:17][C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)=[C:20]([CH3:35])[CH:19]=2)[C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:10][CH:11]=1)=[O:6]

Participants

6

Reactant 4

HCID 947NitrogenHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 86625173HCID 86625173, compound

Product 1

HCID 24969711HCID 24969711, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-[1-(4′-tert-Butyl-2,6-dimethyl-biphenyl-4-ylsulfanyl)-2,2-dimethyl-propyl]-thiophene-2-carboxylic acid cyanomethyl-amide (Isomer 1) (220 mg, 0.436 mmol) in toluene (8.7 mL) is treated with triethylamine hydrochloride (300 mg, 2.18 mmol) and sodium azide (142 mg, 2.18 mmol), then heated at reflux overnight (thermal conditions) or alternatively, placed in a CEM microwave reactor for 20 min (300 W, 180° C., N2 cooling) (microwave conditions). After cooling to room temperature, the reaction mixture is partitioned between ethyl acetate and water. The aqueous layer is back-extracted with ethyl acetate, and the combined organic layers are dried and concentrated to give the title compound (105 mg). MS (ES): 548.3 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight (thermal conditions)
  3. customthe reaction mixture is partitioned between ethyl acetate and water
  4. extractionThe aqueous layer is back-extracted with ethyl acetate
  5. customthe combined organic layers are dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f0e5f554cb6413496aea319d3f643d1
Source dataset
uspto-grants-2010_10
Patent number
US07807702B2

Reaction notes

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